Reassignment of the absolute configuration of the baker's yeast reduction of (+/-)-ethyl 1-allyl-2-oxocyclopentanecarboxylate

Authors
Allan, MM Ramsden, PD Burke, MJ Parvez, M Keay, BA
Citation
Mm. Allan et al., Reassignment of the absolute configuration of the baker's yeast reduction of (+/-)-ethyl 1-allyl-2-oxocyclopentanecarboxylate, TETRAHEDR-A, 10(16), 1999, pp. 3099-3101
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
16
Year of publication
1999
Pages
3099 - 3101
Database
ISI
SICI code
0957-4166(19990813)10:16<3099:ROTACO>2.0.ZU;2-A
Abstract
The baker's yeast reduction of(+/-)-ethyl 1-allyl-2-oxocyclopentanecarboxyl ate under aqueous conditions in the presence of CuO yields (1S,2S)-(+)-ethy l 1-allyl-2-hydroxycyclopentanecarboxylate and the unreacted enantiomer (1R )-(-)-ethyl 1-allyl-2-oxocyclopentanecarboxylate. The absolute configuratio n of the secondary alcohol was determined from the X-ray crystal structure of the (1S)- 10-camphorsulfonyl derivative of (1S,2S)-(+)-ethyl 1-allyl-2-h ydroxycyclopentanecarboxylate. This refutes configurational claims based on CD/ORD and chemical affiliation techniques currently reported in the liter ature for this reaction. (C) 1999 Elsevier Science Ltd. All rights reserved .