Chiral-auxiliary-controlled diastereoselectivity in the epoxidation of enecarbamates with DMD and mCPBA

被引：26

作者：

Adam, W ^{[1
]}

Bosio, SG ^{[1
]}

Wolff, BT ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol0273194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Graphics Chiral oxazolidinone-substituted enecarbamates 1 are epoxidized in a diastereoselectivity up to 93:7 for both DMD and mCPBA. The diastereofacial differentiation depends on the steric interaction between the R-1 substituent on the oxazolidinone ring and the incoming electrophile. The stereochemical course of epoxidation was assessed by chemical correlation with the known optically active diols.

引用

页码：819 / 822

页数：4

共 21 条

[1] Highly diastereoselective dioxetane formation in the photooxygenation of enecarbamates with an oxazolidinone chiral auxiliary: Steric control in the [2+2] cycloaddition of singlet oxygen through conformational alignment [J].

Adam, W ;

Bosio, SG ;

Turro, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (30) :8814-8815

[2] Control of the mode selectivity (ene reaction versus [2+2] cycloaddition) in the photooxygenation of ene carbamates: Directing effect of an alkenylic nitrogen functionality [J].

Adam, W ;

Bosio, SG ;

Turro, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14004-14005

[3] Diastereoselective epoxidation of oxazolidine-substituted alkenes by dimethyldioxirane and m-chloroperbenzoic acid:: π-facial control through hydrogen bonding by the urea functionality [J].

Adam, W ;

Schambony, SB .

ORGANIC LETTERS, 2001, 3 (01) :79-82

[4] Diastereoselective singlet oxygen ene reaction (Schenck reaction) and diastereoselective epoxidations of heteroatom-substituted acyclic chiral olefins: A mechanistic comparison [J].

Adam, W ;

Brunker, HG ;

Kumar, AS ;

Peters, EM ;

Peters, K ;

Schneider, U ;

vonSchnering, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (08) :1899-1905

[5]

Adam W, 1997, LIEBIGS ANN-RECL, P547

[6] Opposite π-face selectivity for the DMD and m-CPBA epoxidations of chiral 2,2-dimethyloxazolidine derivatives of tiglic amides:: Control by steric interactions versus hydrogen bonding [J].

Adam, W ;

Pastor, A ;

Peters, K ;

Peters, EM .

ORGANIC LETTERS, 2000, 2 (08) :1019-1022

[7] Transition state stereoelectronics in alkene epoxidations by fluorinated dioxiranes [J].

Armstrong, A ;

Washington, I ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (26) :6297-6298

[8]

ARMSTRONG A, 2001, J CHEM SOC P1, V21, P2861

[9] High-level computational study of the stereoelectronic effects of substituents on alkene epoxidations with peroxyformic acid [J].

Bach, RD ;

Glukhovtsev, MN ;

Gonzalez, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9902-9910

[10] EPOXIDATION OF ALKENES BY DIMETHYLDIOXIRANE - EVIDENCE FOR A SPIRO TRANSITION-STATE [J].

BAUMSTARK, AL ;

MCCLOSKEY, CJ .

TETRAHEDRON LETTERS, 1987, 28 (29) :3311-3314

← 1 2 3 →