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

被引：65

作者：

Adam, W

Bosio, SG

Turro, NJ

机构：

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

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 30期

关键词：

D O I：

10.1021/ja026815k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The photooxygenation of oxazolidinone-substituted enecarbamates leads to diastereomerically pure dioxetanes. The high diastereoselectivity is rationalized in terms of effective π-facial control achieved by shielding one side of the double bond with the chiral auxiliary. The absolute configuration of the dioxetanes is assigned by derivatization to diols. Copyright © 2002 American Chemical Society.

引用

收藏

页码：8814 / 8815

页数：2

相关论文

共 11 条

[1] Diastereoselective and regioselective singlet-oxygen ene reaction of oxazolidine-substituted alkenes: Control through hydrogen bonding mediated by the urea functionality of chiral auxiliaries [J].

Adam, W ;

Peters, K ;

Peters, EM ;

Schambony, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (31) :7610-7611

[2] A highly diastereoselective dioxetane formation by the hydroxy-directed [2+2] cycloaddition of singlet oxygen to a chiral allylic alcohol [J].

Adam, W ;

Saha-Möller, CR ;

Schambony, SB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) :1834-1838

[3] Chiral-auxiliary-induced diastereoselectivity in the [4+2] cycloadditions of optically active 2,2-dimethyloxazolidine derivatives of sorbic acid:: A model study with singlet oxygen as the smallest dienophile [J].

Adam, W ;

Güthlein, M ;

Peters, EM ;

Peters, K ;

Wirth, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (17) :4091-4093

[4] SYNTHESIS OF THE 2,3-EPOXY-2,3-DIHYDRO-2,3-DIMETHYLBENZO[B]FURAN, THE PROPOSED ULTIMATE MUTAGEN OF THE BENZOFURAN DIOXETANES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

MOSANDL, T ;

SAHAMOLLER, CR ;

WILD, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (02) :200-202

[5]

Ager DJ, 1997, ALDRICHIM ACTA, V30, P3

[6] SYNTHESIS OF A C,D-RING FRAGMENT OF ARTEMISININ [J].

AVERY, MA ;

JENNINGSWHITE, C ;

CHONG, WKM .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1789-1792

[7] NEW PROCEDURE FOR THE DIRECT GENERATION OF TITANIUM ENOLATES - DIASTEREOSELECTIVE BOND CONSTRUCTIONS WITH REPRESENTATIVE ELECTROPHILES [J].

EVANS, DA ;

URPI, F ;

SOMERS, TC ;

CLARK, JS ;

BILODEAU, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8215-8216

[8] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[9] Lithiated 4-isopropyl-3-(methylthiomethyl)-5,5-diphenyloxazolidin-2-one:: A chiral formyl anion equivalent for enantioselective preparations of 1,2-diols, 2-amino alcohols, 2-hydroxy esters, and 4-hydroxy-2-alkenoates [J].

Gaul, C ;

Schärer, K ;

Seebach, D .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3059-3073

[10]

GOLLNICK K, 1981, OXYGEN OXY RADICALS, P379