Journal
ORGANIC LETTERS
Volume 18, Issue 1, Pages 36-39Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03127
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Funding
- National Institute of General Medical Sciences [R01 GM103855]
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An organocatalytic three-component reductive coupling reaction between dimethyl phosphite, benzylidene pyruvates, and aldehydes is reported. A chiral triaryliminophosphorane catalyst promotes Pudovik addition, which is followed by phospha-Brook rearrangement to transiently generate enolates that are trapped stereoselectively by aldehydes. This reductive coupling provides vicinal polyfunctionalized stereocenters from readily available pro chiral starting materials with excellent diastereoselectivity, enantioselectivity, and yield.
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