Asymmetric diene cyclization/hydrosilylation/oxidation employing 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane

Authors
Pei, T Widenhoefer, RA
Citation
T. Pei et Ra. Widenhoefer, Asymmetric diene cyclization/hydrosilylation/oxidation employing 1-tert-butyl-3,3-dimethyl-1,1-diphenyldisiloxane, TETRAHEDR L, 41(40), 2000, pp. 7597-7600
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
40
Year of publication
2000
Pages
7597 - 7600
Database
ISI
SICI code
0040-4039(20000930)41:40<7597:ADCE1>2.0.ZU;2-B
Abstract
A 1:1 mixture of (N-N)Pd(Me)Cl [N-N = (R)-(+)-4-isopropyl-2-(2-pyridinyl)-2 -oxazoline] (1) and NaBAr4 [Ar = 3,5-C6H3(CF3)(2)] catalyzed the asymmetric cyclization/hydrosilylation of functionalized 1,6-dienes with 1-tert-butyl -3,3-dimethyl-1,1-diphenyldisiloxane at -20 degrees C to form silylated cyc lopentanes in good yield with up to 95% ee. These silylated carbocycles und erwent oxidative cleavage of the C-Si bond with H2O2 at room temperature to form the corresponding alcohols. (C) 2000 Elsevier Science Ltd. All rights reserved.