Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization

Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. T...

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2007-09, Vol.2007 (15), p.2375-2378
Main Authors: Schmidt, Bernd, Biernat, Anne
Format: Article
Language:English
Subjects:
letter
Citations: 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-c340t-14a801d9f0f6f3514a36e51486cb212d7b641281a57f84fbe3bd1227687bc1cf3
cites
container_end_page 2378
container_issue 15
container_start_page 2375
container_title Synlett
container_volume 2007
creator Schmidt, Bernd
Biernat, Anne
description Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. The synthesis of di­hydrofurans requires a selective double-bond isomerization on the homoallylic alcohol stage, prior to O-allylation and RCM or RCM-isomerization.
doi_str_mv 10.1055/s-2007-985606
format article
fullrecord <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_2007_985606</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_2007_985606</sourcerecordid><originalsourceid>FETCH-LOGICAL-c340t-14a801d9f0f6f3514a36e51486cb212d7b641281a57f84fbe3bd1227687bc1cf3</originalsourceid><addsrcrecordid>eNp1UMtOwzAQtBBIlMKRuz8Agx-J4xxReFUqooL2HDmJTV01duVNDuHEp5O2cOSyoxnN7qwGoWtGbxlN0zsgnNKM5CqVVJ6gCUtENkq5PEUTmgtJUs6Sc3QBsKGUJSqnE_T9MfhubcABDhY_eu07F1oTXa232wEv-mjwg1sPTQy2j9oD1r75U3bDQbExtLgIbRs8XkRT9xFCBLwC5z_xe_F6WFmOw7R7SmZwSPjSY5S_RGdWb8Fc_eIUrZ4el8ULmb89z4r7OalFQjvCEq0oa3JLrbQiHamQZgQl64oz3mSVTBhXTKeZVYmtjKgaxnkmVVbVrLZiisjxbh0DQDS23EXX6jiUjJb7-koo9_WVx_pG_83R362daU25CX3044P_2H8Aah5yrQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization</title><source>Thieme Connect Journals</source><creator>Schmidt, Bernd ; Biernat, Anne</creator><creatorcontrib>Schmidt, Bernd ; Biernat, Anne</creatorcontrib><description>Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. The synthesis of di­hydrofurans requires a selective double-bond isomerization on the homoallylic alcohol stage, prior to O-allylation and RCM or RCM-isomerization.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-2007-985606</identifier><language>eng</language><subject>letter</subject><ispartof>Synlett, 2007-09, Vol.2007 (15), p.2375-2378</ispartof><rights>Georg Thieme Verlag Stuttgart · New York</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c340t-14a801d9f0f6f3514a36e51486cb212d7b641281a57f84fbe3bd1227687bc1cf3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2007-985606.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2007-985606$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Schmidt, Bernd</creatorcontrib><creatorcontrib>Biernat, Anne</creatorcontrib><title>Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization</title><title>Synlett</title><addtitle>Synlett</addtitle><description>Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. The synthesis of di­hydrofurans requires a selective double-bond isomerization on the homoallylic alcohol stage, prior to O-allylation and RCM or RCM-isomerization.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNp1UMtOwzAQtBBIlMKRuz8Agx-J4xxReFUqooL2HDmJTV01duVNDuHEp5O2cOSyoxnN7qwGoWtGbxlN0zsgnNKM5CqVVJ6gCUtENkq5PEUTmgtJUs6Sc3QBsKGUJSqnE_T9MfhubcABDhY_eu07F1oTXa232wEv-mjwg1sPTQy2j9oD1r75U3bDQbExtLgIbRs8XkRT9xFCBLwC5z_xe_F6WFmOw7R7SmZwSPjSY5S_RGdWb8Fc_eIUrZ4el8ULmb89z4r7OalFQjvCEq0oa3JLrbQiHamQZgQl64oz3mSVTBhXTKeZVYmtjKgaxnkmVVbVrLZiisjxbh0DQDS23EXX6jiUjJb7-koo9_WVx_pG_83R362daU25CX3044P_2H8Aah5yrQ</recordid><startdate>20070917</startdate><enddate>20070917</enddate><creator>Schmidt, Bernd</creator><creator>Biernat, Anne</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20070917</creationdate><title>Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization</title><author>Schmidt, Bernd ; Biernat, Anne</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c340t-14a801d9f0f6f3514a36e51486cb212d7b641281a57f84fbe3bd1227687bc1cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schmidt, Bernd</creatorcontrib><creatorcontrib>Biernat, Anne</creatorcontrib><collection>CrossRef</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schmidt, Bernd</au><au>Biernat, Anne</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2007-09-17</date><risdate>2007</risdate><volume>2007</volume><issue>15</issue><spage>2375</spage><epage>2378</epage><pages>2375-2378</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>Abstract Starting from glyceraldehyde, structurally and stereo­chemically diverse dihydrofurans and dihydropyrans with a 1,2-dihydroxyethylene side chain can be accessed in few steps via allyl metal addition, O-allylation and ring-closing metathesis (RCM) or tandem RCM-isomerization, respectively. The synthesis of di­hydrofurans requires a selective double-bond isomerization on the homoallylic alcohol stage, prior to O-allylation and RCM or RCM-isomerization.</abstract><doi>10.1055/s-2007-985606</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0936-5214
ispartof Synlett, 2007-09, Vol.2007 (15), p.2375-2378
issn 0936-5214
1437-2096
language eng
recordid cdi_crossref_primary_10_1055_s_2007_985606
source Thieme Connect Journals
subjects letter
title Synthesis of Enantiomerically Pure Dihydrofurans and Dihydropyrans from Common Precursors Using RCM and Tandem RCM-Isomerization
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T14%3A36%3A35IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Enantiomerically%20Pure%20Dihydrofurans%20and%20Dihydropyrans%20from%20Common%20Precursors%20Using%20RCM%20and%20Tandem%20RCM-Isomerization&rft.jtitle=Synlett&rft.au=Schmidt,%20Bernd&rft.date=2007-09-17&rft.volume=2007&rft.issue=15&rft.spage=2375&rft.epage=2378&rft.pages=2375-2378&rft.issn=0936-5214&rft.eissn=1437-2096&rft_id=info:doi/10.1055/s-2007-985606&rft_dat=%3Cthieme_cross%3E10_1055_s_2007_985606%3C/thieme_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c340t-14a801d9f0f6f3514a36e51486cb212d7b641281a57f84fbe3bd1227687bc1cf3%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