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Enantioselective synthesis of chiral 5-carbamoyl-3-pyridyl alcohols by asymmetric autocatalytic reaction

✍ Scribed by Takanori Shibata; Hiroshi Morioka; Shigehisa Tanji; Tadakatsu Hayase; Yasutaka Kodaka; Kenso Soai

Book ID: 104255827
Publisher: Elsevier Science
Year: 1996
Tongue: French
Weight: 207 KB
Volume: 37
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02031-x

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✦ Synopsis

A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbamoylpyridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86% e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide.

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