aza-prins-pinalcol approach to 7-azabicyclo[2.2.1]heptanes and ring expansion to [3.2.1]tropanes

被引：21

作者：

Armstrong, A ^{[1
]}

Shanahan, SE ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol0501267

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 7-azabicyclo[2.2.1]heptane ring system can be rapidly accessed from 5-(1-hydroxyallyl)-2-alkoxy-N-tosylpyrrolidines via an unusual aza-Prins-pinacol reaction mediated by Lewis acid. The products can undergo ring expansion to isomeric tropanones. These reactions show promise for a concise entry to biologically relevant azabicyclic targets.

引用

页码：1335 / 1338

页数：4

共 17 条

[1] Aminative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans:: a novel stereocontrolled route to substituted pyrrolidines [J].

Armstrong, A ;

Cumming, GR ;

Pike, K .

CHEMICAL COMMUNICATIONS, 2004, (07) :812-813

[2] TOTAL SYNTHESIS OF EPIBATIDINE [J].

BROKA, CA .

TETRAHEDRON LETTERS, 1993, 34 (20) :3251-3254

[3] A TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-EPIBATIDINE [J].

CLAYTON, SC ;

REGAN, AC .

TETRAHEDRON LETTERS, 1993, 34 (46) :7493-7496

[4] SOLVOLYTIC GENERATION OF ALPHA-SULFONYL AND ALPHA-SULFINYL CARBOCATIONS [J].

CREARY, X ;

MEHRSHEIKHMOHAMMADI, ME ;

EGGERS, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2435-2442

[5] Lewis acid induced tandem Diels-Alder reaction/ring expansion as an equivalent of a [4+3] cycloaddition [J].

Davies, HML ;

Dai, X .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2692-2693

[6] TOTAL SYNTHESIS AND DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF EPIBATIDINE [J].

FLETCHER, SR ;

BAKER, R ;

CHAMBERS, MS ;

HERBERT, RH ;

HOBBS, SC ;

THOMAS, SR ;

VERRIER, HM ;

WATT, AP ;

BALL, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1771-1778

[7]

Gademann K, 2002, ANGEW CHEM INT EDIT, V41, P3059, DOI 10.1002/1521-3773(20020816)41:16<3059::AID-ANIE3059>3.0.CO

[8]

2-I

[9] STEREOCONTROLLED PREPARATION OF TETRAHYDROFURANS FROM ACID-PROMOTED REARRANGEMENTS OF ALLYLIC ACETALS [J].

HOPKINS, MH ;

OVERMAN, LE ;

RISHTON, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5354-5365

[10] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .18. SCOPE AND MECHANISM OF TANDEM CATIONIC AZA-COPE REARRANGEMENT-MANNICH CYCLIZATION REACTIONS [J].

JACOBSEN, EJ ;

LEVIN, J ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4329-4336

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