Preparation of syn-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates

syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt)3]2 with ketones and following desilylation and partial hydrogenation. High diastereoselectivity was observed when arom...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2010-05, Vol.12 (9), p.1968-1971
Hauptverfasser: Yatsumonji, Yasutaka, Sugita, Takenori, Tsubouchi, Akira, Takeda, Takeshi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1971
container_issue 9
container_start_page 1968
container_title Organic letters
container_volume 12
creator Yatsumonji, Yasutaka
Sugita, Takenori
Tsubouchi, Akira
Takeda, Takeshi
description syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt)3]2 with ketones and following desilylation and partial hydrogenation. High diastereoselectivity was observed when aromatic and α,β-unsaturated ketones were employed.
doi_str_mv 10.1021/ol100395n
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_733934187</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>733934187</sourcerecordid><originalsourceid>FETCH-LOGICAL-a314t-3f3f2f1dc35a940f299eb6bc4577fbf5a49641e2ee00e7d279a4ef5c7683f2c23</originalsourceid><addsrcrecordid>eNptkctOGzEUQK0K1ATooj9QeYNQFwN-jOPMEkU8KiGBUFiPPJ5rcOTYqe2pNP0UfoP_4JtqCM2KjW1dHZ_7Qug7JaeUMHoWHCWEN8J_QVMqGK8kEWxv956RCTpIaUUILZHmK5owwoWQNZui57sIGxVVtsHjYHAafbWEmK2KI74O66CcG53V-Nzp8BRcwg_ZOvvX-scScuBHl21WPmjwkPBVOYsMetyN-B76QWf7B_DyDdnleH2pltGuIT-NLtmi38RQanh8z7NQsQuFhXSE9o1yCb593Ifo4fJiubiubm6vfi3ObyrFaZ0rbrhhhvaaC9XUxLCmgW7W6VpIaTojVN3MagoMgBCQPZONqsEILWfz8lEzfohOtt5Sxu8BUm7XNmlwTnkIQ2ol5w2v6VwW8ueW1DGkFMG0m9JHmVRLSfu2iXa3icL--LAO3Rr6Hfl_9AU43gJKp3YVhuhLk5-I_gHFKZWA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>733934187</pqid></control><display><type>article</type><title>Preparation of syn-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates</title><source>American Chemical Society Publications</source><creator>Yatsumonji, Yasutaka ; Sugita, Takenori ; Tsubouchi, Akira ; Takeda, Takeshi</creator><creatorcontrib>Yatsumonji, Yasutaka ; Sugita, Takenori ; Tsubouchi, Akira ; Takeda, Takeshi</creatorcontrib><description>syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt)3]2 with ketones and following desilylation and partial hydrogenation. High diastereoselectivity was observed when aromatic and α,β-unsaturated ketones were employed.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol100395n</identifier><identifier>PMID: 20355742</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2010-05, Vol.12 (9), p.1968-1971</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a314t-3f3f2f1dc35a940f299eb6bc4577fbf5a49641e2ee00e7d279a4ef5c7683f2c23</citedby><cites>FETCH-LOGICAL-a314t-3f3f2f1dc35a940f299eb6bc4577fbf5a49641e2ee00e7d279a4ef5c7683f2c23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol100395n$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol100395n$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20355742$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yatsumonji, Yasutaka</creatorcontrib><creatorcontrib>Sugita, Takenori</creatorcontrib><creatorcontrib>Tsubouchi, Akira</creatorcontrib><creatorcontrib>Takeda, Takeshi</creatorcontrib><title>Preparation of syn-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt)3]2 with ketones and following desilylation and partial hydrogenation. High diastereoselectivity was observed when aromatic and α,β-unsaturated ketones were employed.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNptkctOGzEUQK0K1ATooj9QeYNQFwN-jOPMEkU8KiGBUFiPPJ5rcOTYqe2pNP0UfoP_4JtqCM2KjW1dHZ_7Qug7JaeUMHoWHCWEN8J_QVMqGK8kEWxv956RCTpIaUUILZHmK5owwoWQNZui57sIGxVVtsHjYHAafbWEmK2KI74O66CcG53V-Nzp8BRcwg_ZOvvX-scScuBHl21WPmjwkPBVOYsMetyN-B76QWf7B_DyDdnleH2pltGuIT-NLtmi38RQanh8z7NQsQuFhXSE9o1yCb593Ifo4fJiubiubm6vfi3ObyrFaZ0rbrhhhvaaC9XUxLCmgW7W6VpIaTojVN3MagoMgBCQPZONqsEILWfz8lEzfohOtt5Sxu8BUm7XNmlwTnkIQ2ol5w2v6VwW8ueW1DGkFMG0m9JHmVRLSfu2iXa3icL--LAO3Rr6Hfl_9AU43gJKp3YVhuhLk5-I_gHFKZWA</recordid><startdate>20100507</startdate><enddate>20100507</enddate><creator>Yatsumonji, Yasutaka</creator><creator>Sugita, Takenori</creator><creator>Tsubouchi, Akira</creator><creator>Takeda, Takeshi</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100507</creationdate><title>Preparation of syn-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates</title><author>Yatsumonji, Yasutaka ; Sugita, Takenori ; Tsubouchi, Akira ; Takeda, Takeshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-3f3f2f1dc35a940f299eb6bc4577fbf5a49641e2ee00e7d279a4ef5c7683f2c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yatsumonji, Yasutaka</creatorcontrib><creatorcontrib>Sugita, Takenori</creatorcontrib><creatorcontrib>Tsubouchi, Akira</creatorcontrib><creatorcontrib>Takeda, Takeshi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yatsumonji, Yasutaka</au><au>Sugita, Takenori</au><au>Tsubouchi, Akira</au><au>Takeda, Takeshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of syn-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2010-05-07</date><risdate>2010</risdate><volume>12</volume><issue>9</issue><spage>1968</spage><epage>1971</epage><pages>1968-1971</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>syn-Tertiary homoallylic alcohols were obtained by the reaction of α-silylallenyltitanocenes generated by the reductive titanation of γ-silylpropargylic carbonates with Cp2Ti[P(OEt)3]2 with ketones and following desilylation and partial hydrogenation. High diastereoselectivity was observed when aromatic and α,β-unsaturated ketones were employed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20355742</pmid><doi>10.1021/ol100395n</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2010-05, Vol.12 (9), p.1968-1971
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_733934187
source American Chemical Society Publications
title Preparation of syn-Tertiary Homoallylic Alcohols Utilizing Allenyltitanocenes Generated by Reductive Titanation of γ-Trimethylsilylpropargylic Carbonates
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T11%3A04%3A18IST&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=Preparation%20of%20syn-Tertiary%20Homoallylic%20Alcohols%20Utilizing%20Allenyltitanocenes%20Generated%20by%20Reductive%20Titanation%20of%20%CE%B3-Trimethylsilylpropargylic%20Carbonates&rft.jtitle=Organic%20letters&rft.au=Yatsumonji,%20Yasutaka&rft.date=2010-05-07&rft.volume=12&rft.issue=9&rft.spage=1968&rft.epage=1971&rft.pages=1968-1971&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol100395n&rft_dat=%3Cproquest_cross%3E733934187%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=733934187&rft_id=info:pmid/20355742&rfr_iscdi=true