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Conformational effects on lipase-mediated acylations of 2-substituted cyclohexanols

✍ Scribed by Rikuhei Tanikaga; Yoshimasa Matsumoto; Maki Sakaguchi; Yohei Koyama; Kentaro Ono

Book ID: 104254128
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 133 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01514-4

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✦ Synopsis

Lipase-mediated acetylations of trans-and cis-2-substituted cyclohexanols gave the corresponding (1R)-cyclohexyl acetates and (1S)-cyclohexanols in high yields and ee, but c-4-tert-butyl-c-2-ethenyl-r-1-cyclohexanol was unreactive owing to the steric interaction between the axial OH group and the axial H atoms at the 3-and 5-positions. In the cis-isomer the OH group occupies an equatorial position to bind to the lipase, and less bulky axial alkenyl and alkynyl groups might not so much prevent acetylations than an alkyl group.

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