cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines

被引：54

作者：

O'Brien, P ^{[1
]}

Childs, AC ^{[1
]}

Ensor, GJ ^{[1
]}

Hill, CL ^{[1
]}

Kirby, JP ^{[1
]}

Dearden, MJ ^{[1
]}

Oxenford, SJ ^{[1
]}

Rosser, CM ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 26期

关键词：

D O I：

10.1021/ol035873n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better cis directors than sulfonamides or carbamates) whereas di-N-protected systems gave trans-epoxides (TsNBoc protection gave complete trans stereoselectivity).

引用

页码：4955 / 4957

页数：3

共 21 条

[1] EPOXIDATION OF PRIMARY AND SECONDARY ALKENYLAMMONIUM SALTS WITH DIMETHYLDIOXIRANE, METHYL(TRIFLUOROMETHYL) DIOXIRANE, AND M-CHLOROPERBENZOIC ACID - A GENERAL SYNTHETIC ROUTE TO EPOXYALKYLAMINES [J].

ASENSIO, G ;

MELLO, R ;

BOIXBERNARDINI, C ;

GONZALEZNUNEZ, ME ;

CASTELLANO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3692-3699

[2]

BACKVALL JE, 1979, J ORG CHEM, V44, P1953

[3] STRUCTURE AND SYNTHESIS OF NEW CYCLOPENTENYL ISONITRILES FROM TRICHODERMA-HAMATUM (BON) BAIN AGGR HLX 1379 [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CHONDROGIANNI, J ;

EDENBOROUGH, MS ;

KEEPING, JW ;

ZIEGLER, CB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (12) :816-817

[4] Synthesis and reactions of cyclopentadiene monoaziridine: a concise approach to the core of agelastatin A [J].

Baron, E ;

O'Brien, P ;

Towers, TD .

TETRAHEDRON LETTERS, 2002, 43 (04) :723-726

[5] New route to 4-aminocyclopent-2-en-1-ols: Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides [J].

Barrett, S ;

O'Brien, P ;

Steffens, HC ;

Towers, TD ;

Voith, M .

TETRAHEDRON, 2000, 56 (49) :9633-9640

[6] SYNTHESIS AND ENZYMATIC EVALUATION OF CONFORMATIONALLY DEFINED CARNITINE ANALOGS [J].

BROUILLETTE, WJ ;

SAEED, A ;

ABUELYAMAN, A ;

HUTCHISON, TL ;

WOLKOWICZ, PE ;

MCMILLIN, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4297-4303

[7] First synthesis of (-)-neplanocin C [J].

Comin, MJ ;

Rodriguez, JB .

TETRAHEDRON, 2000, 56 (27) :4639-4649

[8]

Demay S, 2001, SYNTHESIS-STUTTGART, P863

[9] 2-NITROBENZENESULFONAMIDES AND 4-NITROBENZENESULFONAMIDES - EXCEPTIONALLY VERSATILE MEANS FOR PREPARATION OF SECONDARY-AMINES AND PROTECTION OF AMINES [J].

FUKUYAMA, T ;

JOW, CK ;

CHEUNG, M .

TETRAHEDRON LETTERS, 1995, 36 (36) :6373-6374

[10] NEIGHBORING GROUPS IN ADDITION .6. THE BENZAMIDO GROUP IN 3-BENZAMIDOCYCLOHEXENE - STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED CYCLOHEXANE DERIVATIVES [J].

GOODMAN, L ;

WINSTEIN, S ;

BOSCHAN, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (16) :4312-4317

← 1 2 3 →