Journal
TETRAHEDRON LETTERS
Volume 56, Issue 17, Pages 2265-2268Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.03.063
Keywords
Allylic substitution; Palladium; Enolate; Stereoselectivity; Regioselectivity
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Funding
- Ministry of Education, Science, Sports, and Culture, Japan
- Grants-in-Aid for Scientific Research [26410111] Funding Source: KAKEN
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Palladium-catalyzed allylic substitution of unsymmetrically substituted secondary allylic esters with eight enolate anions derived from ketones and an ester was examined to find that the substitution of the phosphate esters with lithium enolates proceeded regioselectively. The stereochemical course of the substitution was studied using enantiomerically enriched allylic phosphate to confirm retention of the stereochemistry. The cyclic version of the allylic phosphate afforded substitution products with the same sense of the regio- and stereoselectivity. (C) 2015 Elsevier Ltd. All rights reserved.
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