Journal
ORGANIC LETTERS
Volume 12, Issue 8, Pages 1664-1667Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100075m
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Funding
- National Science Foundation [CHE-0911483, CHE-0722547]
- Oakland University
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0821487] Funding Source: National Science Foundation
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In this paper, the development of a chiral phosphine-catalyzed formal [2 + 2] cycloaddition of aldehydes and ketoketenes that provides access to a variety of highly substituted beta-lactones (14 examples) is reported. The BINAPHANE catalytic system displays excellent enantioselectivity (seven examples with ee >= 90%) and high diastereoselectivity favoring formation of the trans-diastereomer (nine examples with dr >= 90:10).
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