Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes

A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Ad...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2023-12, Vol.88 (23), p.16666-16670
Main Authors: Hart, Alison P., DeGraw, Caroline J., Rustin, Gavin J., Donahue, Matthew G., Pigza, Julie A.
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-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133
cites cdi_FETCH-LOGICAL-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133
container_end_page 16670
container_issue 23
container_start_page 16666
container_title Journal of organic chemistry
container_volume 88
creator Hart, Alison P.
DeGraw, Caroline J.
Rustin, Gavin J.
Donahue, Matthew G.
Pigza, Julie A.
description A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Adducts are then unmasked, providing various oxidation state 3 functional groups, thereby highlighting the utility of these MAC reagents and a new strategy for the preparation of β-amino acids.
doi_str_mv 10.1021/acs.joc.3c01838
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2890360942</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2890360942</sourcerecordid><originalsourceid>FETCH-LOGICAL-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133</originalsourceid><addsrcrecordid>eNotkM1KAzEUhYMoWKtrt1m6mTb_kyxL8Q-qFdR1uM0kMnU6aZPpYnwsH8Rnckp7NgcO51wuH0K3lEwoYXQKLk_W0U24I1RzfYZGVDJSKEPEORoRwljBmeKX6CrnNRkkpRyht_fdHhJs6srjZfqCNjrooOl_fIVnVVV3dWxxDBjwC-TvQ-j6Bs97aA-LLuK_3-K17lLMXZ986_M1ugjQZH9z8jH6fLj_mD8Vi-Xj83y2KBwrRVeUTHgVVkYpB9KTMki90tQQJ0sG3shgpDImaC5BeyFLLp0yXABbMaME5XyM7o53tynu9j53dlNn55sGWh_32TJtCFfECDZUp8eqG97MyQe7TfUGUm8psQd2dmBnB3b2xI7_A1jDY34</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2890360942</pqid></control><display><type>article</type><title>Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Hart, Alison P. ; DeGraw, Caroline J. ; Rustin, Gavin J. ; Donahue, Matthew G. ; Pigza, Julie A.</creator><creatorcontrib>Hart, Alison P. ; DeGraw, Caroline J. ; Rustin, Gavin J. ; Donahue, Matthew G. ; Pigza, Julie A.</creatorcontrib><description>A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Adducts are then unmasked, providing various oxidation state 3 functional groups, thereby highlighting the utility of these MAC reagents and a new strategy for the preparation of β-amino acids.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.3c01838</identifier><language>eng</language><ispartof>Journal of organic chemistry, 2023-12, Vol.88 (23), p.16666-16670</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133</citedby><cites>FETCH-LOGICAL-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133</cites><orcidid>0000-0002-1289-5679</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Hart, Alison P.</creatorcontrib><creatorcontrib>DeGraw, Caroline J.</creatorcontrib><creatorcontrib>Rustin, Gavin J.</creatorcontrib><creatorcontrib>Donahue, Matthew G.</creatorcontrib><creatorcontrib>Pigza, Julie A.</creatorcontrib><title>Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes</title><title>Journal of organic chemistry</title><description>A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Adducts are then unmasked, providing various oxidation state 3 functional groups, thereby highlighting the utility of these MAC reagents and a new strategy for the preparation of β-amino acids.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNotkM1KAzEUhYMoWKtrt1m6mTb_kyxL8Q-qFdR1uM0kMnU6aZPpYnwsH8Rnckp7NgcO51wuH0K3lEwoYXQKLk_W0U24I1RzfYZGVDJSKEPEORoRwljBmeKX6CrnNRkkpRyht_fdHhJs6srjZfqCNjrooOl_fIVnVVV3dWxxDBjwC-TvQ-j6Bs97aA-LLuK_3-K17lLMXZ986_M1ugjQZH9z8jH6fLj_mD8Vi-Xj83y2KBwrRVeUTHgVVkYpB9KTMki90tQQJ0sG3shgpDImaC5BeyFLLp0yXABbMaME5XyM7o53tynu9j53dlNn55sGWh_32TJtCFfECDZUp8eqG97MyQe7TfUGUm8psQd2dmBnB3b2xI7_A1jDY34</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Hart, Alison P.</creator><creator>DeGraw, Caroline J.</creator><creator>Rustin, Gavin J.</creator><creator>Donahue, Matthew G.</creator><creator>Pigza, Julie A.</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1289-5679</orcidid></search><sort><creationdate>20231201</creationdate><title>Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes</title><author>Hart, Alison P. ; DeGraw, Caroline J. ; Rustin, Gavin J. ; Donahue, Matthew G. ; Pigza, Julie A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hart, Alison P.</creatorcontrib><creatorcontrib>DeGraw, Caroline J.</creatorcontrib><creatorcontrib>Rustin, Gavin J.</creatorcontrib><creatorcontrib>Donahue, Matthew G.</creatorcontrib><creatorcontrib>Pigza, Julie A.</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hart, Alison P.</au><au>DeGraw, Caroline J.</au><au>Rustin, Gavin J.</au><au>Donahue, Matthew G.</au><au>Pigza, Julie A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes</atitle><jtitle>Journal of organic chemistry</jtitle><date>2023-12-01</date><risdate>2023</risdate><volume>88</volume><issue>23</issue><spage>16666</spage><epage>16670</epage><pages>16666-16670</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A method for the squaramide-organocatalyzed enantioselective addition of a silyl-protected masked acyl cyanide (MAC) reagent to various β-nitrostyrenes is described. Reactions are carried out in a freezer and provide products cleanly and in high enantioselectivities at very low catalyst loadings. Adducts are then unmasked, providing various oxidation state 3 functional groups, thereby highlighting the utility of these MAC reagents and a new strategy for the preparation of β-amino acids.</abstract><doi>10.1021/acs.joc.3c01838</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1289-5679</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2023-12, Vol.88 (23), p.16666-16670
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2890360942
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Squaramide Organocatalyzed Addition of a Masked Acyl Cyanide to β-Nitrostyrenes
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T20%3A42%3A21IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Squaramide%20Organocatalyzed%20Addition%20of%20a%20Masked%20Acyl%20Cyanide%20to%20%CE%B2-Nitrostyrenes&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Hart,%20Alison%20P.&rft.date=2023-12-01&rft.volume=88&rft.issue=23&rft.spage=16666&rft.epage=16670&rft.pages=16666-16670&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.3c01838&rft_dat=%3Cproquest_cross%3E2890360942%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c274t-724e6fb966ca5e07f58b8190c572ae95f95699f835a8e45735c6934a2b2964133%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2890360942&rft_id=info:pmid/&rfr_iscdi=true