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Stereoselective reduction of α-alkoxy acetylenic ketones with zinc borohydride and K-selectride.

✍ Scribed by Takashi Takahashi; Masahiro Miyazawa; Jiro Tsuji

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
188 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reduction of a-benzyloxy acetylenic ketones with zinc borohydride afforded the erythro-acetylenic vicinal diols in 95% stereoselectivity, while reduction with K-selectride gave the isomeric threo-diols in 90% stereoselectivity.

Repetition of 1,3-chiral transfer reaction by palladium catalyzed allylationl), coupling reaction of organocuprate2), and [3,3]-or [2,3]-sigmatropic rearrangements of allylic compounds3), as shown in scheme 1, offer a powerful method for construction of the vicinal carbon asymmetric centers. Scheme 1 2 1

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