Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine
Keyword(s):
X Ray
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AbstractThe first enzyme-catalyzed kinetic resolution of tert-butyl-3-hydroxy-4-phenylpyrrolidine-1-carboxylate is presented. Enzyme, solvent and temperature optimization resulted in a new resolution method with E = 40 enantioselectivity. The acetate derivative of the (+)-(3S,4R) enantiomer formed while the (−)-(3R,4S) isomer remained intact. Very good enantioselectivities (E > 200) were achieved in the enzyme-catalyzed alcoholysis of the racemic acetate in i-propanol and t-butanol where the (+)-(3S,4R) enantiomer was prepared in pure form (ee > 99.7%). Absolute configuration of the (−)-(3R,4S)-enantiomer was determined by single crystal X-ray diffraction method.
1997 ◽
Vol 212
(3)
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Keyword(s):
2017 ◽
Vol 28
(10)
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pp. 1330-1336
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2014 ◽
Vol 70
(a1)
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pp. C1560-C1560
2015 ◽
Vol 73
(7)
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pp. 755-761
2000 ◽
Vol 38
(2-3)
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pp. 403-412
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2015 ◽
Vol 48
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pp. 853-856
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