A new strategy for synthesis of attached rings

被引：37

作者：

Overman, LE ^{[1
]}

Pennington, LD ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2000年 / 78卷 / 06期

关键词：

Prins cyclization; pinacol rearrangement; attached rings;

D O I：

10.1139/cjc-78-6-732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first investigation of the use of pinacol-terminated Prins cyclizations to form attached rings is reported. Treatment of triisopropylsilyl ethers of (Z)- or (E)-[2-(6,6-dimethoxyhexylidene)cyclohexanol with SnCl4 provides bicyclic products having attached rings. The approach is synthetically useful in the Z alkylidenecyclohexane series, proceeding selectively by a pathway involving carbon migration in the pinacol rearrangement step, to provide methoxy epimers of 1-(2-methoxycyclohexyl)cyclopentylcarboxaldehyde. Reaction of the corresponding E stereoisomer is more complex and yields a mixture of products resulting from both hydride and carbon migration in the pinacol rearrangement step.

引用

收藏

页码：732 / 738

页数：7

相关论文

共 41 条

[1] Ring-enlarging cyclohexane annulations [J].

Ando, S ;

Minor, KP ;

Overman, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6379-6387

[2] STEREOCHEMISTRY AND MECHANISM OF PINACOL-TYPE REARRANGEMENTS IN 1-PHENYL-4-TERT-BUTYLCYCLOHEXANE SERIES [J].

BARILI, PL ;

BERTI, G ;

MACCHIA, B ;

MACCHIA, F ;

MONTI, L .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (09) :1168-&

[3]

BARTOK M, 1980, CHEM ETHERS CROWN 2

[4]

Brickmann K, 1996, LIEBIGS ANN, P457

[5] ACID-PROMOTED REACTION OF CYCLIC ALLYLIC DIOLS WITH CARBONYL-COMPOUNDS - STEREOSELECTIVE RING-ENLARGING TETRAHYDROFURAN ANNULATIONS [J].

BROWN, MJ ;

HARRISON, T ;

HERRINTON, PM ;

HOPKINS, MH ;

HUTCHINSON, KD ;

MISHRA, P ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5365-5378

[6] GENERAL-APPROACH TO HALOGENATED TETRAHYDROFURAN NATURAL-PRODUCTS FROM RED ALGAE OF THE GENUS LAURENCIA - TOTAL SYNTHESIS OF (+/-)-TRANS-KUMAUSYNE AND DEMONSTRATION OF AN ASYMMETRIC-SYNTHESIS STRATEGY [J].

BROWN, MJ ;

HARRISON, T ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5378-5384

[7] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[8] Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].

Cloninger, MJ ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093

[9] STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES [J].

DENMARK, SE ;

WEBER, EJ ;

WILSON, TM ;

WILLSON, TM .

TETRAHEDRON, 1989, 45 (04) :1053-1065

[10] THE STEREOSTRUCTURES OF [1,1'-BICYCLOHEXYL]-2,2'-DIONES - A REASSIGNMENT [J].

DENMARK, SE ;

CRAMER, CJ ;

STERNBERG, JA .

TETRAHEDRON LETTERS, 1986, 27 (32) :3693-3696

← 1 2 3 4 5 →