Allenoate prenucleophiles: a triply diastereoselective approach to beta-hydroxy esters containing all-carbon alpha-quaternary centers
Title | Allenoate prenucleophiles: a triply diastereoselective approach to beta-hydroxy esters containing all-carbon alpha-quaternary centers |
Publication Type | Journal Article |
Year of Publication | 2019 |
Authors | Maki, SL, Maity, P, Dougherty, S, Johns, J, Lepore, SD |
Journal | Organic Letters |
Volume | 21 |
Issue | 19 |
Pagination | 7952-7955 |
Date Published | OCT |
Type of Article | Article |
ISSN | 1523-7060 |
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. |
DOI | 10.1021/acs.orglett.9b02930 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 6.555 |
Divison category:
Organic Chemistry
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