STEREOSELECTIVE APPROACH TO TRISUBSTITUTED TETRAHYDROFURANS

被引：44

作者：

MOHR, P

机构：

[1] Pharmaceutical Research Department, F. Hoffmann-La Roche Ltd

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 39期

关键词：

ALLYLSILANE; TETRAHYDROFURAN; 1,3-INDUCTION; RING CLOSURE;

D O I：

10.1016/S0040-4039(00)73723-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized allylsilanes 1 undergo with acetals 2 under mild Broensted acid catalysis a transacetalization-ring closure reaction to afford in fair to good yield and high diastereoselectivity all-cis-tetrahydrofurans 3. The stereochemical outcome is independent of the double bond geometry.

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页码：6251 / 6254

页数：4

相关论文

共 15 条

[1] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].

AOKI, S ;

MIKAMI, K ;

TERADA, M ;

NAKAI, T .

TETRAHEDRON, 1993, 49 (09) :1783-1792

[2] 5-MEMBERED RING ANNULATION VIA PROPARGYLSILANES AND ALLYLSILANES [J].

DANHEISER, RL ;

DIXON, BR ;

GLEASON, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6094-6097

[3] ON THE STEREOCHEMISTRY OF ALLYLMETAL-ALDEHYDE CONDENSATIONS [J].

DENMARK, SE ;

WEBER, EJ .

HELVETICA CHIMICA ACTA, 1983, 66 (06) :1655-1660

[4]

Fleming I., 1989, ORG REACTIONS, V37, P57

[5] CYCLIC TRANSITION-STATE IN THE ACID-CATALYZED INTRAMOLECULAR ALLYLSTANNANE-ALDEHYDE CONDENSATION [J].

GEVORGYAN, V ;

KADOTA, I ;

YAMAMOTO, Y .

TETRAHEDRON LETTERS, 1993, 34 (08) :1313-1316

[6] CHARACTERISTICS IN THE REACTIONS OF ALLYLSILANES AND THEIR APPLICATIONS TO VERSATILE SYNTHETIC EQUIVALENTS [J].

HOSOMI, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (05) :200-206

[7]

ITOH A, 1979, TETRAHEDRON LETT, V20, P1783

[8]

LARSON GL, 1989, CHEM ORGANOSILICON C, pCH11

[9] STEREOSELECTIVE SYNTHESIS OF SYN-1,3-DIOLS [J].

MOHR, P .

TETRAHEDRON LETTERS, 1992, 33 (18) :2455-2458

[10] CONJUGATE ADDITION-REACTIONS OF CHIRAL (E)-CROTYLSILANES - APPLICATION TO AN ASYMMETRIC [3+2] CYCLOPENTANE ANNULATION [J].

PANEK, JS ;

JAIN, NF .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2345-2348