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Enantioselective Synthesis of Both Enantiomers of Various Propargylic Alcohols by Use of Two Oxidoreductases
Author(s) -
Schubert Thomas,
Hummel Werner,
Kula MariaRegina,
Müller Michael
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200111)2001:22<4181::aid-ejoc4181>3.0.co;2-t
Subject(s) - enantiopure drug , chemistry , enantioselective synthesis , enantiomeric excess , candida parapsilosis , yield (engineering) , alcohol dehydrogenase , steric effects , enantiomer , organic chemistry , alcohol , catalysis , diastereomer , lactobacillus brevis , antifungal , medicine , lactic acid , materials science , dermatology , lactobacillus plantarum , biology , bacteria , metallurgy , genetics
The oxidoreductases Lactobacillus brevis alcohol dehydrogenase (LBADH) and Candida parapsilosis carbonyl reductase (CPCR) are suitable catalysts for the reduction of ketones to afford enantiopure sec. alcohols. A broad variety of alkynones ( 1 , 3 , and 5 ) are accepted as substrates and the corresponding propargylic alcohols ( 2 , 4 , and 6 ) are obtained in good yield and excellent enantiomeric excess. By changing the steric demand of the substituents the ee values can be adjusted and even the configurations of the products can be altered.