Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans

被引：36

作者：

Cohen, F ^{[1
]}

MacMillan, DWC ^{[1
]}

Overman, LE ^{[1
]}

Romero, A ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 08期

关键词：

D O I：

10.1021/ol0157003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

引用

收藏

页码：1225 / 1228

页数：4

相关论文

共 25 条

[1]

BARTOK M, 1980, CHEM ETHERS CROWN 2, P722

[2] CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD [J].

BROEKER, JL ;

HOFFMANN, RW ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5006-5017

[3] 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

[4] 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

[5] STEREOMUTATION OF METHOXYCARBENIUM IONS .1. AN INVESTIGATION OF THE MECHANISM IN GASEOUS AND SOLUTION PHASES [J].

CREMER, D ;

GAUSS, J ;

CHILDS, RF ;

BLACKBURN, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (08) :2435-2441

[6] GENERAL-APPROACH TO HALOGENATED TETRAHYDROFURAN NATURAL-PRODUCTS FROM RED ALGAE OF THE GENUS LAURENCIA - TOTAL SYNTHESIS OF (+/-)-KUMAUSALLENE AND (+/-)-1-EPI-KUMAUSALLENE [J].

GRESE, TA ;

HUTCHINSON, KD ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2468-2477

[7] A CORRELATION OF REACTION RATES [J].

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) :334-338

[8] Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral [J].

Hanaki, N ;

Link, JT ;

MacMillan, DWC ;

Overman, LE ;

Trankle, WG ;

Wurster, JA .

ORGANIC LETTERS, 2000, 2 (02) :223-226

[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] THEORY AND MODELING OF STEREOSELECTIVE ORGANIC-REACTIONS [J].

HOUK, KN ;

PADDONROW, MN ;

RONDAN, NG ;

WU, YD ;

BROWN, FK ;

SPELLMEYER, DC ;

METZ, JT ;

LI, Y ;

LONCHARICH, RJ .

SCIENCE, 1986, 231 (4742) :1108-1117