DIASTEREOSELECTIVE ADDITION OF ALLYLTRIPHENYL-STANNANE TO 3-SULFINYLFURFURAL MEDIATED BY TITANIUM(IV) TETRACHLORIDE AND TIN(IV) TETRACHLORIDE

被引：18

作者：

ARAI, Y ^{[1
]}

MASUDA, T ^{[1
]}

MASAKI, Y ^{[1
]}

KOIZUMI, T ^{[1
]}

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,TOYAMA,TOYAMA 93001,JAPAN

来源：

HETEROCYCLES | 1994年 / 38卷 / 08期

关键词：

D O I：

10.3987/COM-94-6801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of allyltriphenylstannane to 3-sulfinylfurfural (3) in the presence of titanium(IV) tetrachloride proceeded with high diastereoselectivity to give the furyl alcohol (6), whereas the similar treatment with tin(IV) tetrachloride afforded the other diastereoisomeric alcohol (7), exclusively.

引用

页码：1751 / 1756

页数：6

共 30 条

[1] ARAI Y, 1992, REV HETEROATOM CHEM, V6, P202
[2] ENZYMATIC RESOLUTION OF SOME HIGHER ALPHA-AMINO ACIDS AND PREPARATION OF OPTICALLY ACTIVE ALPHA-HYDROXY ACIDS
BAKER, CG
MEISTER, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (03) : 1336 - 1338
[3] ASYMMETRIC CARBON CARBON BOND FORMATION VIA BETA-ALLYLDIISOPINOCAMPHEYLBORANE - SIMPLE SYNTHESIS OF SECONDARY HOMOALLYLIC ALCOHOLS WITH EXCELLENT ENANTIOMERIC PURITIES
BROWN, HC
JADHAV, PK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) : 2092 - 2093
[4] ASYMMETRIC ALLYLBORATION OF ACYLSILANES
BUYNAK, JD
GENG, BL
UANG, SN
STRICKLAND, JB
[J]. TETRAHEDRON LETTERS, 1994, 35 (07) : 985 - 988
[5] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
COREY, EJ
YU, CM
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496
[6] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS
COSTA, AL
PIAZZA, MG
TAGLIAVINI, E
TROMBINI, C
UMANIRONCHI, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7001 - 7002
[7] SYNTHESES OF ENANTIOMERICALLY PURE FURYL AND THIENYL PARA-TOLYL SULFOXIDES
GIRODIER, L
MAIGNAN, C
ROUESSAC, F
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (07) : 857 - 858
[8] PROTECTING GROUP CONTROLLED DIASTEREOSELECTIVE ALLYLATION OF ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDES (BHYMA-STAR)
GUANTI, G
BANFI, L
NARISANO, E
[J]. TETRAHEDRON LETTERS, 1991, 32 (47) : 6939 - 6942
[9] ENANTIOSELECTIVE ALLYLTITANATION OF ALDEHYDES WITH CYCLOPENTADIENYLDIALKOXYALLYLTITANIUM COMPLEXES
HAFNER, A
DUTHALER, RO
MARTI, R
RIHS, G
ROTHESTREIT, P
SCHWARZENBACH, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) : 2321 - 2336
[10] ALKOXYVINYL THIONIUM IONS IN INTRAMOLECULAR 4+3 CYCLOADDITION REACTIONS
HARMATA, M
FLETCHER, VR
CLAASSEN, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) : 9861 - 9862

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