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1.3.1.7.1.2 Synthesis of Chiral Secondary Alcohols

DOI: 10.1055/sos-SD-214-00086

Bertau, M.; Jeromin, G. E.Science of Synthesis: Biocatalysis in Organic Synthesis, (20151164.

The enzymatic kinetic resolution of esters of chiral secondary alcohols by hydrolysis with esterases and lipases has been systematically investigated. It was found that the stereoselectivity of the reactions with cholesterol esterase and Pseudomonas cepacia lipase follows Kazlauskasʼ rule (see Scheme 33, Section 1.3.1.4.2).[‌92‌]

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Meeeeeeeeee 88

M Meeeeeeeee (%) ee (%) Mee
Me 88 88 [‌88‌]
(MM8)8Me 88 88 [‌88‌]
(MM8)8MM=MMe8 88 88 [‌88‌]

Meeeeeeeeee 88M

M8 Meeeeeeeee (%) ee (%) Mee
Me 88 88 [‌88‌]
MMe 88 88 [‌88‌]
MM 88 88 [‌88‌]

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Meeeeeeeeee 88

M8 eM Meeeee ee Meeeeee ee (%) ee Meeeee Meeee Mee
MM8Me 8.8 M 88 [‌88‌]
MM 8.8 M 88 [‌88‌]
Me 8.8 M 88 [‌88‌]

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Meeeee 88 Meeeeeeee Meeeeeeeee ee α-Meeeeee Meeeee Meeeeee eeee MMM[‌888‌]

Meeeeeeeeee 88

e Meee (e) ee (%) ee (M)-88 Meeee (%) ee (M)-88 Mee
8 8 88 88 [‌888‌]
8 8 88 88 [‌888‌]

Meeeeeeeeee 88M

e Meee (e) (M)-88 (M)-88 Mee
ee (%) Meeee (%) ee (%) Meeee (%)
8 8 88 88 88 88 [‌888‌]
8 8 88 88 88 88 [‌888‌]

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Meeeee 88 Meeeeeeeeeeeeeeeee ee eee Meeeeeeeee ee M-Meeeeeeeeeee ee Meeeeeeeeee eeeeeee Meeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee (%) Meeeeee Meeeeeee ee (%) Mee
M Me  8 [‌88‌]
Me Me 88 (M)-88 <88 [‌88‌]
e-Me Me 88 (M)-88 88 [‌88‌]
e-Me M(M)Me 88 (M)-88 >88 [‌88‌]

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Meeeee 88 Meeeeeeee Meeeeeeeee ee Meeeeeeee α- eee β-Meeeeeeeeeeeeeee eeee Meeeee Meeee M[‌888‌]

Meeeeeeeeee 88

e Meee (e) Meeeeeeeee (%) (M)-88 (M)-88 Mee
ee (%) Meeee (%) ee (%) Meeee (%)
8 88 88 88 88 88 88 [‌888‌]
8 88 88 88 88 88 88 [‌888‌]

Meeeeeeeeee 88M

e Meee (e) Meeeeeeeee (%) (M)-88 (M)-88 Mee
ee (%) Meeee (%) ee (%) Meeee (%)
8 88 88 88 88 88 88 [‌888‌]
8 88 88 88 88 88 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

(M)-8-Meeeeeeeeee Meeeeee [(M)-88] eee (M)-8-Meeeeeeeeeeee [(M)-88]:[‌888‌]

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References