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1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) Catalyzed Regiospecific and Diastereoselective Reaction of Chiral N-(tert-Butanesulfinyl)ketimines and α,β-Unsaturated Trifluoromethyl Ketones

✍ Scribed by Fan Zhang; Zhenjiang Liu; Jintao Liu

Book ID: 102096982
Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 95 KB
Volume: 29
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.201100133

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✦ Synopsis

Abstract

The reaction of chiral N‐(tert‐butanesulfinyl)ketimines and α,β‐unsaturated trifluoromethyl ketones catalyzed by DBU was achieved under mild conditions. 1,2‐Addition products, precursors of chiral trifluoromethylated 1,3‐amino alcohols, were obtained diastereoselectively (dr value up to 95:5) in moderate yields (up to 76%). A possible catalytic cycle was proposed.

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