A NOVEL CHIRAL BUILDING-BLOCK WITH NEOPEN TANE FRAMEWORK FOR SYNTHESIS - CHEMOENZYMATIC PREPARATION OF (R)-CH3C(CH2OSO2CF3)(CH2CL)(CH2BR)

Authors
HEIDEL H HUTTNER G VOGEL R HELMCHEN G
Citation
H. Heidel et al., A NOVEL CHIRAL BUILDING-BLOCK WITH NEOPEN TANE FRAMEWORK FOR SYNTHESIS - CHEMOENZYMATIC PREPARATION OF (R)-CH3C(CH2OSO2CF3)(CH2CL)(CH2BR), Chemische Berichte, 127(1), 1994, pp. 271-274
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Chemische Berichte → ACNP
ISSN journal
00092940
Volume
127
Issue
1
Year of publication
1994
Pages
271 - 274
Database
ISI
SICI code
0009-2940(1994)127:1<271:ANCBWN>2.0.ZU;2-E
Abstract
The pig liver esterase (PLE) catalysed hydrolysis of the prochiral mal onic ester (BzlOCH(2)) (Me)C(COOMe)(2) (1) leads to its chiral monoest er 2 in selectivities up to 81% ee. Compound 2 is an ideal entry point for the enantioselective synthesis of 1,1',1''-substituted neopentane s CH3C(CH(2)X)- (CH2Y)(CH(2)Z) with three different leaving groups, X, Y, and Z. CH3C(CH2OSO2CF3)(CH2Br) (CH2Cl) (8) is a versatile reactive building block for the asymmetric synthesis of compounds containing t he neopentane-C-5 skeleton.