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Diastereoselective reduction and carboncarbon bond formation of α-keto esters/amides with SmI2

✍ Scribed by Shin-ichi Fukuzawa; Manabu Miura; Hiroshi Matsuzawa

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
70 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereoselective reduction of a-keto esters/a-keto amides, which have various chiral auxiliaries using SmI 2 , is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)-and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding a-hydroxy ester and amide in good diastereoselectivity with satisfactory yields. Allylation, the Reformatsky-type reaction, and the ketyl-alkene coupling reaction with the 1,1,2(R)-triphenylethanediol and 2(S)-methoxymethylpyrrolidine, derivative of the a-keto ester/amide proceeded smoothly with high diastereoselectivity.

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