Dilithiated 3-tosylpropanal dimethyl acetal as beta,beta-acylvinyl dianion or homoenolate dianion equivalent

被引：20

作者：

Bonete, P ^{[1
]}

Najera, C ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIA,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(96)00072-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,3-Dilithio-1,1-dimethoxy-3-tosylpropane (6) reacts with mono and dielectrophiles to give dialkylated products 7 and carbocyclic derivatives 8, respectively. Hydrolysis of the acetal function followed by DBU dehydrosulfinylation of these products affords beta,beta-disubstituted propenal derivatives 11 and 12. Reductive desulfonylation of compounds 8g-j provides beta,beta-disubstituted propanal acetals 14.

引用

页码：4111 / 4122

页数：12

共 20 条

[1] LITHIATED 5-TOSYLPROPANAL AND 4-TOSYL-2-BUTANONE DIMETHYL ACETALS AS BETA-ACYLVINYL ANION EQUIVALENTS FOR THE SYNTHESIS OF UNSATURATED 1,4-DICARBONYL COMPOUNDS AND ALPHA,BETA-BUTENOLIDES
BONETE, P
NAJERA, C
[J]. TETRAHEDRON, 1995, 51 (09) : 2763 - 2776
[2] LITHIUM 3-LITHIO-3-TOSYLALKANOATES - BETA-ACYLVINYL ANION EQUIVALENTS OF BETA-LITHIATED ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS
BONETE, P
NAJERA, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) : 3202 - 3209
[3] LITHIUM 3-LITHIO-3-TOSYLPROPANOATE - A USEFUL ALPHA-TOSYLATED HOMOENOLATE ANION
BONETE, P
NAJERA, C
[J]. TETRAHEDRON LETTERS, 1992, 33 (28) : 4065 - 4068
[4] SYNTHESIS OF CYCLOHEXYLIDENEACETALDEHYDE AND 2-METHYLCYCLOHEXYLIDENEACETALDEHYDE, 3-METHYLCYCLOHEXYLIDENEACETALDEHYDE AND 4-METHYLCYCLOHEXYLIDENEACETALDEHYDE
CHACO, MC
IYER, BH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (02) : 186 - 190
[5] SULFONE REAGENTS IN ORGANIC-SYNTHESIS .7. [(PHENYLSULFONYL)METHYLENE]DILITHIUM AS A NOVEL CYCLIZING AND HOMOLOGIZING REAGENT FOR BIFUNCTIONAL ORGANIC SUBSTRATES
EISCH, JJ
DUA, SK
BEHROOZ, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) : 3674 - 3676
[6] A CONCEPTUALLY NEW ROUTE TO OPTICALLY-ACTIVE CARBA-PROSTACYCLINS - SYNTHESIS OF EXOCYCLIC ALKENES VIA DOUBLY LITHIATED ALLYL SULFONES
GAIS, HJ
BALL, WA
BUND, J
[J]. TETRAHEDRON LETTERS, 1988, 29 (07) : 781 - 784
[7] GAIS HJ, 1985, ANGEW CHEM INT EDIT, V24, P608
[8] STEREOCHEMICAL DEPENDENCE OF THE BIS-ALKYLATION REACTION OF ALPHA,ALPHA-DILITHIATED ALLYL PHENYL SULFONE WITH CIS- AND TRANS-1,4-DICHLORO-2-BUTENE - A CONVENIENT METHOD FOR THE SYNTHESIS OF A CYCLOHEPTA-1,4-DIENE SYSTEM
HOUSTON, TA
KOREEDA, M
[J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (03) : 393 - 398
[9] KAISER EM, 1977, SYNTHESIS-STUTTGART, P509
[10] THE DIAZO ROUTE TO 2-VINYLCYCLOPROPYLIDENES
KIRMSE, W
VANCHIEM, P
HENNING, PG
[J]. TETRAHEDRON, 1985, 41 (08) : 1441 - 1451

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