Tetrahedron p. 4747 - 4758 (1985)
Update date:2022-08-04
Topics: Stereochemistry Optically active Asymmetric Oxidation Allyl Achiral Selenides Selenoxides Sigmatropic rearrangement
Davis, Franklin A.
Stringer, Orum D.
McCauley, John P., Jr.
Asymmetric oxidation of methyl phenyl selenide (3), under anhydrous conditions, by chiral 2-sulfonyloxaziridines, 1-2, give optically active methyl phenyl selenoxide (8.1-9.3percent ee).The stereochemistry of the selenoxide is determined by the configuration of the oxaziridine three membered ring with nonbonded steric interactions responsible for the chiral recognition.Asymmetric oxidation of E-phenyl cinnamyl selenide (7) by 1-2 affords optically active 1-phenylallyl alcohol (9).A concerted <2,3> sigmatropic rearrangement via an exo transition state is proposed.
View Morewebsite:http://www.josunpharma.com
Contact:+86-311-80715268 80766839
Address:No.39, Zhaiying Street, Shijaizhuang,Hebei,China
SHANDONG QINGYUNCHANGXIN CHEMICAL SCIENCE-TECH CO.,LTD
Contact:86-21-60560171
Address:1689Donghuan Rade,Qingyun County, Dezhou City, Shandong,China
Contact:+86-571-86025531 / 86024803
Address:1218-24 Guangyin Mansion,42 Fengqi East Road
Yangling Ciyuan biotech Co., Ltd.
Contact:86-15802970736
Address:2-1804, International Park Mansion, No.2, South Fengdeng Road, Lianhu District
Shijiazhuang Yunxuan Im&Export Co.,Ltd.
Contact:+86-311-83037514
Address:No.6 Hongbin Road
Doi:10.1016/S0040-4020(01)96683-9
(1985)Doi:10.1016/j.tetlet.2008.03.151
(2008)Doi:10.1002/jhet.5570450322
(2008)Doi:10.1002/hlca.19620450627
(1962)Doi:10.1002/hlca.200890072
(2008)Doi:10.1021/jo902641g
(2010)
