Ammonium directed dihydroxylation of N, N-dibenzylaminocyclohex-2-ene:: metal-free syntheses of the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane

被引：16

作者：

Davies, SG ^{[1
]}

Long, MJC ^{[1
]}

Smith, AD ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Organ Chem, Oxford OX1 3TA, England

来源：

CHEMICAL COMMUNICATIONS | 2005年 / 36期

关键词：

D O I：

10.1039/b509088a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of N,N-dibenzylaminocyclohex-2-ene with mCPBA in the presence of CCl3CO2H gives 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-N,N-dibenzylaminocyclohexane with high diastereoselectivity; this methodology has been used to facilitate the metal-free stereoselective syntheses of all the diastereoisomers of 3-dibenzylamino-1,2-dihydroxycyclohexane.

引用

页码：4536 / 4538

页数：3

共 33 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] H-bonding interactions in the epoxidation of alkenylammonium salts with dimethyldioxirane and m-chloroperbenzoic acid:: A kinetic study [J].

Asensio, G ;

Boix-Bernardini, C ;

Andreu, C ;

González-Núñez, ME ;

Mello, R ;

Edwards, JO ;

Carpenter, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4705-4711

[3] REGIOSELECTIVE OXYFUNCTIONALIZATION OF UNACTIVATED TERTIARY AND SECONDARY C-H BONDS OF ALKYLAMINES BY METHYL(TRIFLUOROMETHYL)DIOXIRANE IN ACID-MEDIUM [J].

ASENSIO, G ;

GONZALEZNUNEZ, ME ;

BERNARDINI, CB ;

MELLO, R ;

ADAM, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7250-7253

[4]

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

[5] 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

[6] EPOXIDATION OF ALLYLIC ALCOHOLS WITH PEROXY-ACIDS - ATTEMPTS TO DEFINE TRANSITION STATE GEOMETRY [J].

CHAMBERL.P ;

ROBERTS, ML ;

WHITHAM, GH .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07) :1374-&

[7] Oxidative functionalisation of SuperQuat enamides: Asymmetric synthesis of homochiral 1,2 diols [J].

Davies, SG ;

Key, MS ;

Rodriguez-Solla, H ;

Sanganee, HJ ;

Savory, ED ;

Smith, AD .

SYNLETT, 2003, (11) :1659-1662

[8] STEREOCHEMICAL ASPECTS OF THE VANADIUM-CATALYZED EPOXIDATION OF CONFORMATIONALLY BIASED CYCLOHEX-2-EN-1-OLS BY ALKYL HYDROPEROXIDES [J].

DEHNEL, RB ;

WHITHAM, GH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (04) :953-955

[9] Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA [J].

Donohoe, TJ ;

Blades, K ;

Moore, PR ;

Waring, MJ ;

Winter, JJG ;

Helliwell, M ;

Newcombe, NJ ;

Stemp, G .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (23) :7946-7956

[10] A new approach to functionalised spiropiperidines through tandem RCM and nitrogen-directed reactions [J].

Edwards, AS ;

Wybrow, RAJ ;

Johnstone, C ;

Adams, H ;

Harrity, JPA .

CHEMICAL COMMUNICATIONS, 2002, (14) :1542-1543

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