@article{e8d1fc5e2e714683872dd66247dc92f6,
title = "Highly anti-diastereoselective reduction of 2-alkyl-3-oxo amides by potassium triethylborohydride",
abstract = "Potassium triethylborohydride was found to reduce 2-alkyl-3-oxo amides to the corresponding 3-hydroxy amides with excellent anti-diastereoselectivity (>99:1), and in combination with asymmetric acylation, a useful route to optically active anti-2-alkyl-3-hydroxy acids was developed.",
author = "Yoshio Ito and Tsutomu Katsuki and Masaru Yamaguchi",
note = "Funding Information: A typical example of the reduction is given below. A solution of potassium triethylborohydride (1 mol dms3, 125 1~1, 1.1 eq) in THF was added slowly to an ether solution (1.2 ml) of (25,52,2'S)-N-2',4'-dimethyl-3'-oxovaleryl-2,5-bis(methoxymethoxymethyl)pyrrolidine ') (39-.3 mg I 0.11 mmol) at 0°C. After stirring for a few min at the same temperature, aqueous phosphoric acid (3%, 0.2 ml) was added. Extraction (CH2C12), drying (Na2S04), evaporation, and column chromatography (silica gel) gave (2S,SS,2'S,3'S)-z-2', 4'-dimethyl-3'-hydroxyvaleryl-2,5-bis(methoxymethoxymethyl)pyrrolidine (39.1 mg, 99%). The work was partially supported by the Grand-in Aid for Special Project Research (No. 58110006) from the Ministry of Education, Science, and Culture, Japan. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",
year = "1985",
doi = "10.1016/S0040-4039(00)98774-4",
language = "English",
volume = "26",
pages = "4643--4646",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "38",
}