Allenoate prenucleophiles: a triply diastereoselective approach to beta-hydroxy esters containing all-carbon alpha-quaternary centers

TitleAllenoate prenucleophiles: a triply diastereoselective approach to beta-hydroxy esters containing all-carbon alpha-quaternary centers
Publication TypeJournal Article
Year of Publication2019
AuthorsMaki, SL, Maity, P, Dougherty, S, Johns, J, Lepore, SD
JournalOrganic Letters
Volume21
Issue19
Pagination7952-7955
Date PublishedOCT
Type of ArticleArticle
ISSN1523-7060
Abstract

Allenyl esters activated by titanium(IV) underwent additions to a wide range of aldehydes in high regio- and diastereoselectivities leading to products containing an all carbon quaternary center bearing an alpha-vinyl group that was installed with high selectivity for the Z-geometry. An aldol product was also converted to an indanone offering a new route to this important compound class. Product triple diastereoselectivity has been rationalized using a concerted transition-state model.

DOI10.1021/acs.orglett.9b02930
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

6.555

Divison category: 
Organic Chemistry

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