Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 23, Pages 9411-9416Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8019863
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Funding
- Department of Science and Technology, India
- Council of Scientific and Industrial Research, New Delhi
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We report the synthesis of a new series of highly efficient chiral organocatalysts derived via the regio- and stereoselective ring opening of chiral aziridines with azide anions. The catalysts have proved to be very efficient for it direct asymmetric aldol reaction, both with cyclic as well as acyclic ketones in brine with 2 mol % of catalyst loading, and afforded the products in excellent yields (up to 99%) and enantioselectivities (up to >99%). The chiral aldol adduct obtained has further been converted to a chiral azetidine ring via a convenient pathway.
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