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Stereoselective reduction of 3-oxo amides with zinc borohydride

✍ Scribed by Yoshio Ito; Masaru Yamaguchi

Book ID: 104221285
Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 137 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87875-2

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✦ Synopsis

2-Alkyl-3-oxo amides were reduced to the corresponding syn-2-alkyl-3-hydroxy amides with high stereoselectivity by zinc borohydride. In the search for new stereoselective reducing agents, T. Nakata and T. .ll Oishi found that the reduction of 4-unsaturated (phenyl or carbon-carbon double bond) 2-alkyl-3-oxo esters with Zn(BH4)2 in ether gave syn-2-alkyl-3-hydroxy esters almost exclusively. 2) They suggested that the high stereoselectivity of the reaction may be due to the conformational fixation by six-membered chelate ring formation which was promoted by the enhanced donating ability of a conjugated 3-0x0 group. 3) In fact, the reduction of the saturated analogues did not give good selectivity. 11

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