Enantioselective Diels-Alder reaction with an α-chloronitroso dienophile derived from 5-O-acetyl-2,3-isopropylidenedioxy-D-ribose

被引：0

作者：

Defoin, A ^{[1
]}

Joubert, M ^{[1
]}

Heuchel, JM ^{[1
]}

Strehler, C ^{[1
]}

Streith, J ^{[1
]}

机构：

[1] Univ Haute Alsace, Ecole Natl Super Chim Mulhouse, F-68093 Mulhouse, France

来源：

SYNTHESIS-STUTTGART | 2000年 / 12期

关键词：

asymmetric Diels-Alder reaction; 1,2-oxazines; D-ribose derivatives; chloronitroso dienophiles; heterocycles;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Crystalline 5-O-acetyl-2,3-isopropylidenedioxy-D-ribonolactone oxime (8) was synthesised from D-ribose in 40% overall yield. The chloronitroso dienophile 3b was obtained from 8 by oxidation with t-BuOCl and underwent asymmetric Diels-Alder reaction with cyclic and acyclic dienes 10-13 to give crystalline adducts 14a-17a in good yield and excellent enantiomeric excess (93-99%).

引用

页码：1719 / 1726

页数：8

共 56 条

[1]

Adams R., 1939, J AM CHEM SOC, V61, P2083

[2] OXIDATION OF ALDOSE OXIMES - FORMATION AND STRUCTURE OF HYDROXYDIAZENE OXIDE ACETALS AND PREPARATION OF HYDROXIMOLACTONES - X-RAY CRYSTAL-STRUCTURE OF 2,3-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSYL-ONN-AZOXY 2,3-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSIDE [J].

AEBISCHER, BM ;

HANSSEN, HW ;

VASELLA, AT ;

SCHWEIZER, WB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2139-2147

[3] Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8397-8406

[4] Synthesis of an 1-azaglucose analogue with ring-oxygen retained. [J].

Bach, P ;

Bols, M .

TETRAHEDRON LETTERS, 1999, 40 (17) :3461-3464

[5] A NEW ROUTE TO SOME ENANTIOMERICALLY PURE SUBSTITUTED MORPHOLINES FROM D-RIBONO- AND D-GULONO-1,4-LACTONES [J].

BENNIS, K ;

CALINAUD, P ;

GELAS, J ;

GHOBSI, M .

CARBOHYDRATE RESEARCH, 1994, 264 (01) :33-44

[6]

Boger D. L., 1987, HETERO DIELS ALDER M

[7]

BRAUN H, 1993, LIEBIGS ANN CHEM, P261

[8]

BRAUN H, 1987, LIEBIGS ANN CHEM, P1129

[9] ORTHO-ACYLHYDROXYLAMINES .1. SYNTHESIS OF ORTHO-BENZOYLHYDROXYLAMINE [J].

CARPINO, LA ;

GIZA, CA ;

CARPINO, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (04) :955-957

[10] STEREOSELECTIVITY IN THE ENE REACTION OF SYN AND ANTI-1-(4-TERT-BUTYLCYCLOHEXYLIDENE)-4-TERT-BUTYLCYCLOHEXANE WITH SINGLET OXYGEN, NITROSYL HYDRIDE, NITROSOFORMALDEHYDE, 4-PHENYL-1,2,4-TRIAZOL-3,5-DIONE, DIETHYL AZODICARBOXYLATE AND METHYL PROPIOLATE [J].

DANG, HS ;

DAVIES, AG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (05) :721-734

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