Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum

The complex MoTp­(NO)­(DMAP)­(η2-naphthalene) (1; DMAP = 4-(dimethylamino)­pyridine; Tp = tris­(pyrazolyl)­borate) is demonstrated to undergo Michael–Michael ring-closure (MIMIRC) reactions promoted by trimethylsilyltriflate. The resulting hexahydrophenanthrenes are formed stereoselectively, with is...

Full description

Saved in:
Bibliographic Details
Published in:Organometallics 2020-04, Vol.39 (8), p.1404-1412
Main Authors: Myers, Jeffery T, Wilde, Justin H, Sabat, Michal, Dickie, Diane A, Harman, W. Dean
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3
cites cdi_FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3
container_end_page 1412
container_issue 8
container_start_page 1404
container_title Organometallics
container_volume 39
creator Myers, Jeffery T
Wilde, Justin H
Sabat, Michal
Dickie, Diane A
Harman, W. Dean
description The complex MoTp­(NO)­(DMAP)­(η2-naphthalene) (1; DMAP = 4-(dimethylamino)­pyridine; Tp = tris­(pyrazolyl)­borate) is demonstrated to undergo Michael–Michael ring-closure (MIMIRC) reactions promoted by trimethylsilyltriflate. The resulting hexahydrophenanthrenes are formed stereoselectively, with isolation of a single dominant isomer. Combining the MIMIRC sequence with an oxidative decomplexation step, the final tricyclics can be synthesized from the naphthalene complex with overall yields between 19 and 50% (for four steps). This reaction sequence is shown to be capable of producing a steroidal core directly from naphthalene, providing access to a biologically relevant carbon framework.
doi_str_mv 10.1021/acs.organomet.0c00110
format article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_organomet_0c00110</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c905838775</sourcerecordid><originalsourceid>FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3</originalsourceid><addsrcrecordid>eNqFkNtKw0AQhhdRsFYfQdgXSN1Tss2lxEOFVqHodZhsZpuUJBt2U7B3voNv6JOY0uKtVzPDzzfMfITccjbjTPA7MGHm_AY61-IwY4YxztkZmfBYsChhip-TCRM6ibSU8pJchbBljCVaigkpV7WpAJufr-9TR9d1t4myxoWdR7pGMEPtukCt8xToQ11BP7goc86XdQcDlvQV-mqooMEOaebavsFP6ixduWZflNjt2mtyYaEJeHOqU_Lx9PieLaLl2_NLdr-MQKTxEGkjlUKrS5VgiqZQGvW8HCetxk9sKYSyoNMkhiQt1JynqeQ2FnxujQRrCjkl8XGv8S4Ejzbvfd2C3-ec5QdV-agq_1OVn1SNHD9yh3jrdr4br_yH-QXWjHQT</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Myers, Jeffery T ; Wilde, Justin H ; Sabat, Michal ; Dickie, Diane A ; Harman, W. Dean</creator><creatorcontrib>Myers, Jeffery T ; Wilde, Justin H ; Sabat, Michal ; Dickie, Diane A ; Harman, W. Dean</creatorcontrib><description>The complex MoTp­(NO)­(DMAP)­(η2-naphthalene) (1; DMAP = 4-(dimethylamino)­pyridine; Tp = tris­(pyrazolyl)­borate) is demonstrated to undergo Michael–Michael ring-closure (MIMIRC) reactions promoted by trimethylsilyltriflate. The resulting hexahydrophenanthrenes are formed stereoselectively, with isolation of a single dominant isomer. Combining the MIMIRC sequence with an oxidative decomplexation step, the final tricyclics can be synthesized from the naphthalene complex with overall yields between 19 and 50% (for four steps). This reaction sequence is shown to be capable of producing a steroidal core directly from naphthalene, providing access to a biologically relevant carbon framework.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/acs.organomet.0c00110</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organometallics, 2020-04, Vol.39 (8), p.1404-1412</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3</citedby><cites>FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3</cites><orcidid>0000-0003-0939-3309 ; 0000-0003-0939-6980</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Myers, Jeffery T</creatorcontrib><creatorcontrib>Wilde, Justin H</creatorcontrib><creatorcontrib>Sabat, Michal</creatorcontrib><creatorcontrib>Dickie, Diane A</creatorcontrib><creatorcontrib>Harman, W. Dean</creatorcontrib><title>Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum</title><title>Organometallics</title><addtitle>Organometallics</addtitle><description>The complex MoTp­(NO)­(DMAP)­(η2-naphthalene) (1; DMAP = 4-(dimethylamino)­pyridine; Tp = tris­(pyrazolyl)­borate) is demonstrated to undergo Michael–Michael ring-closure (MIMIRC) reactions promoted by trimethylsilyltriflate. The resulting hexahydrophenanthrenes are formed stereoselectively, with isolation of a single dominant isomer. Combining the MIMIRC sequence with an oxidative decomplexation step, the final tricyclics can be synthesized from the naphthalene complex with overall yields between 19 and 50% (for four steps). This reaction sequence is shown to be capable of producing a steroidal core directly from naphthalene, providing access to a biologically relevant carbon framework.</description><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkNtKw0AQhhdRsFYfQdgXSN1Tss2lxEOFVqHodZhsZpuUJBt2U7B3voNv6JOY0uKtVzPDzzfMfITccjbjTPA7MGHm_AY61-IwY4YxztkZmfBYsChhip-TCRM6ibSU8pJchbBljCVaigkpV7WpAJufr-9TR9d1t4myxoWdR7pGMEPtukCt8xToQ11BP7goc86XdQcDlvQV-mqooMEOaebavsFP6ixduWZflNjt2mtyYaEJeHOqU_Lx9PieLaLl2_NLdr-MQKTxEGkjlUKrS5VgiqZQGvW8HCetxk9sKYSyoNMkhiQt1JynqeQ2FnxujQRrCjkl8XGv8S4Ejzbvfd2C3-ec5QdV-agq_1OVn1SNHD9yh3jrdr4br_yH-QXWjHQT</recordid><startdate>20200427</startdate><enddate>20200427</enddate><creator>Myers, Jeffery T</creator><creator>Wilde, Justin H</creator><creator>Sabat, Michal</creator><creator>Dickie, Diane A</creator><creator>Harman, W. Dean</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-0939-3309</orcidid><orcidid>https://orcid.org/0000-0003-0939-6980</orcidid></search><sort><creationdate>20200427</creationdate><title>Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum</title><author>Myers, Jeffery T ; Wilde, Justin H ; Sabat, Michal ; Dickie, Diane A ; Harman, W. Dean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Myers, Jeffery T</creatorcontrib><creatorcontrib>Wilde, Justin H</creatorcontrib><creatorcontrib>Sabat, Michal</creatorcontrib><creatorcontrib>Dickie, Diane A</creatorcontrib><creatorcontrib>Harman, W. Dean</creatorcontrib><collection>CrossRef</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Myers, Jeffery T</au><au>Wilde, Justin H</au><au>Sabat, Michal</au><au>Dickie, Diane A</au><au>Harman, W. Dean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum</atitle><jtitle>Organometallics</jtitle><addtitle>Organometallics</addtitle><date>2020-04-27</date><risdate>2020</risdate><volume>39</volume><issue>8</issue><spage>1404</spage><epage>1412</epage><pages>1404-1412</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>The complex MoTp­(NO)­(DMAP)­(η2-naphthalene) (1; DMAP = 4-(dimethylamino)­pyridine; Tp = tris­(pyrazolyl)­borate) is demonstrated to undergo Michael–Michael ring-closure (MIMIRC) reactions promoted by trimethylsilyltriflate. The resulting hexahydrophenanthrenes are formed stereoselectively, with isolation of a single dominant isomer. Combining the MIMIRC sequence with an oxidative decomplexation step, the final tricyclics can be synthesized from the naphthalene complex with overall yields between 19 and 50% (for four steps). This reaction sequence is shown to be capable of producing a steroidal core directly from naphthalene, providing access to a biologically relevant carbon framework.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.organomet.0c00110</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-0939-3309</orcidid><orcidid>https://orcid.org/0000-0003-0939-6980</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0276-7333
ispartof Organometallics, 2020-04, Vol.39 (8), p.1404-1412
issn 0276-7333
1520-6041
language eng
recordid cdi_crossref_primary_10_1021_acs_organomet_0c00110
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Michael–Michael Ring-Closure Reactions for a Dihapto-Coordinated Naphthalene Complex of Molybdenum
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T20%3A44%3A58IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Michael%E2%80%93Michael%20Ring-Closure%20Reactions%20for%20a%20Dihapto-Coordinated%20Naphthalene%20Complex%20of%20Molybdenum&rft.jtitle=Organometallics&rft.au=Myers,%20Jeffery%20T&rft.date=2020-04-27&rft.volume=39&rft.issue=8&rft.spage=1404&rft.epage=1412&rft.pages=1404-1412&rft.issn=0276-7333&rft.eissn=1520-6041&rft_id=info:doi/10.1021/acs.organomet.0c00110&rft_dat=%3Cacs_cross%3Ec905838775%3C/acs_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a295t-7c344ef7d46e9ecb47e78dd4674520fd224fa7965a69b4819931f5218fc3afcb3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true