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Synthesis 2004(16): 2629-2632  
DOI: 10.1055/s-2004-831197
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Activation of Zinc: Application of the Blaise Reaction to an Expedient Synthesis of a Statin Intermediate

Hyunik Shin*a, Bo Seung Choia, Ki Kon Leea, Hyeong-wook Choia, Jay Hyok Changa, Kyu Woong Leea, Do Hyun Nama, No-Soo Kim*b
a Chemical Development Division, LG Life Sciences, Ltd./R&D, 104-1, Moonji-dong, Yusong-gu, Daejon 305-380, Korea
b Faculty of Life Science Engineering, Youngdong University, San 12-1 Sulkye-ri Yeongdong-eup Yeongdong-gun Chungbuk, Korea
Fax: +82(42)8665754; e-Mail: hisin@lgls.co.kr;
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Publication History

Received 21 May 2004
Publication Date:
26 August 2004 (online)

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Abstract

Efficient and practical in situ zinc activation was accomplished by treatment with catalytic amount of an organic acid. The protocol was applied successfully to the Blaise reaction of various nitriles. Noteworthy is the excellent Blaise transformation of (S)-4-chloro-3-trimethylsilyloxybutyronitrile (2b) into tert-butyl (S)-6-chloro-5-hydroxy-3-oxohexanoate (1), a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins).

Key words

in situ zinc activation - Blaise reaction - statin intermediate

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