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Efficient Asymmetric Synthesis of α-Trifluoromethyl-Substituted Primary Amines via Nucleophilic 1,2-Addition to Trifluoroacetaldehyde SAMP− or RAMP−Hydrazone

✍ Scribed by Enders, Dieter; Funabiki, Kazumasa

Book ID: 127040407
Publisher: American Chemical Society
Year: 2001
Tongue: English
Weight: 41 KB
Volume: 3
Category: Article
ISSN: 1523-7060
DOI: 10.1021/ol015869g

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ChemInform Abstract: Efficient Asymmetri

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A simple and efficient X-step asymmetric synthesis of 6-substituted 6-ketoesters 2 in 45-62% overall chemical yield and Z96--100% ee is described. The key step is an asymmetric Michael-addition of lithiated methylketone-SAMPor RAMP-hydrazones to a,B-unsaturated esters 2 with virtually complete 1.6-