Copper-Catalyzed [gamma]-Selective and Stereospecific Direct Allylic Alkylation of Terminal Alkynes: Synthesis of Skipped Enynes

Skipping out: The title reaction using internal secondary allylic phosphates proceeded with excellent γregioselectivity and Estereoselectivity to give skipped enynes. Enantioenriched secondary allylic phosphates proceeded with 1,3-anti stereochemistry to afford the corresponding chiral 1,4-enynes, w...

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Published inAngewandte Chemie International Edition Vol. 52; no. 20; pp. 5350 - 5354
Main Authors Makida, Yusuke, Takayama, Yurie, Ohmiya, Hirohisa, Sawamura, Masaya
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 10.05.2013
EditionInternational ed. in English
Subjects
Alkylation
Alkynes
Phosphates
Stereochemistry
Synthesis
Terminals
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Summary:Skipping out: The title reaction using internal secondary allylic phosphates proceeded with excellent γregioselectivity and Estereoselectivity to give skipped enynes. Enantioenriched secondary allylic phosphates proceeded with 1,3-anti stereochemistry to afford the corresponding chiral 1,4-enynes, which were used for various derivatizations and the formal total synthesis of a GnRH antagonist. phen=1,10-phenanthroline.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201300785