1,4-asymmetric reduction of gamma-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group

Authors
Nakamura, S Kuroyanagi, M Watanabe, Y Toru, T
Citation
S. Nakamura et al., 1,4-asymmetric reduction of gamma-keto sulfoxides bearing the 2,4,6-triisopropylphenyl group, J CHEM S P1, (18), 2000, pp. 3143-3148
Citations number
47
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
18
Year of publication
2000
Pages
3143 - 3148
Database
ISI
SICI code
1470-4358(2000):18<3143:1ROGSB>2.0.ZU;2-Y
Abstract
Reduction of gamma-keto sulfoxides bearing the 2,4,6-triisopropylphenyl gro up with DIBAL gives gamma-hydroxy sulfoxides with high stereoselectivity in the ratio 95:5. In comparison with the lower stereoselectivities obtained in the reaction of gamma-keto sulfoxides bearing p-tolyl or 2,4,6-trimethyl phenyl groups, the sterically bulky (2,4,6-triisopropylphenyl)sulfinyl grou p is extremely efficient in effecting high 1,4-remote asymmetric induction.