Samarium diiodide-mediated asymmetric reactions of 8-phenylmenthyl esters

Authors
Fang, JM Chen, MY Shiue, JS Lu, L Hsu, JL
Citation
Jm. Fang et al., Samarium diiodide-mediated asymmetric reactions of 8-phenylmenthyl esters, TETRAHEDR L, 41(23), 2000, pp. 4633-4636
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
23
Year of publication
2000
Pages
4633 - 4636
Database
ISI
SICI code
0040-4039(20000612)41:23<4633:SDARO8>2.0.ZU;2-1
Abstract
(-)-8-Phenylmenthol was used as a chiral auxiliary to direct asymmetric rea ctions of its preformed carboxylates. Reduction of xanthates la and Ib by S mI2 likely proceeded via HMPA-bound samarium enolate intermediates. Self- a nd cross-pinacolic coupling reactions of 8-phenylmenthyl alpha-oxoesters we re achieved in a highly stereoselective manner by treatment with SmI2 at -7 8 degrees C. The stereochemical outcome was consistent with a chelated mode of transition states. (C) 2000 Elsevier Science Ltd. All rights reserved.