THE UNSYMMETRICAL SILAKETAL AS A NEUTRAL, REMOVABLE TETHER FOR EFFECTING INTRAMOLECULAR DIELS-ALDER REACTIONS

被引：47

作者：

GILLARD, JW ^{[1
]}

FORTIN, R ^{[1
]}

GRIMM, EL ^{[1
]}

MAILLARD, M ^{[1
]}

TJEPKEMA, M ^{[1
]}

BERNSTEIN, MA ^{[1
]}

GLASER, R ^{[1
]}

机构：

[1] MERCK FROSST CTR THERAPEUT RES,POB 1005,POINTE CLAIRE,QUEBEC,CANADA

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)92029-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silaketals, in which reactive dienes and dienophiles are linked, can participate in intramolecular Diels-Alder reactions to produce products with a high degree of stereocontrol and with regiochemistry opposite to that predicted by bond polarization models.

引用

页码：1145 / 1148

页数：4

共 18 条

[1]

BOECKMAN RK, 1985, J ORG CHEM, V50, P3423

[2] DIISOPROPYLSILYL DITRIFLATE AND DI-TERT-BUTYLSILYL DITRIFLATE - NEW REAGENTS FOR THE PROTECTION OF DIOLS [J].

COREY, EJ ;

HOPKINS, PB .

TETRAHEDRON LETTERS, 1982, 23 (47) :4871-4874

[3] A NOVEL STRATEGY FOR REGIOCONTROL AND STEREOCONTROL IN [4+2] CYCLOADDITIONS - INTRAMOLECULAR DIELS-ALDER REACTION OF A SILYL ACETAL TRIENE [J].

CRAIG, D ;

READER, JC .

TETRAHEDRON LETTERS, 1990, 31 (45) :6585-6588

[4] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

CRAIG, D .

CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238

[5] DERIVATIVES OF 1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE FOR DIELS-ALDER REACTIONS [J].

DANISHEFSKY, S ;

YAN, CF ;

SINGH, RK ;

GAMMILL, RB ;

MCCURRY, PM ;

FRITSCH, N ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7001-7008

[6]

FLUDZINSKI P, ORG SYNTH, V64, P104

[7]

FORTIN R, 1989, 1989 ACS PAC M P

[8]

FRATER G, 1976, TETRAHEDRON LETT, V49, P4517

[9]

FUNK RL, 1984, TETRAHEDRON LETT, V16, P1655

[10] SYMMETRICAL ALKOXYSILYL ETHERS - A NEW CLASS OF ALCOHOL-PROTECTING GROUPS - PREPARATION OF TERT-BUTOXYDIPHENYLSILYL ETHERS [J].

GILLARD, JW ;

FORTIN, R ;

MORTON, HE ;

YOAKIM, C ;

QUESNELLE, CA ;

DAIGNAULT, S ;

GUINDON, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2602-2608

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