MONO AND DILITHIATION OF BENZYL[2-(TOSYLMETHYL)-2-PROPENYL] AMINE - NEW GAMMA-AMINATED ALLYL SULFONE ANIONS

被引：7

作者：

ALONSO, DA ^{[1
]}

NAJERA, C ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)78519-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mono and dilithiation of benzyl-[2-(tosylmethyl)-2-propenyl]amine (4) with n-butyllithium affords the corresponding allylic anions 5a and 5b, respectively. Monoanion 5a reacts regioselectively at the a-position of the sulfone group with deuterium oxide, alkyl halides, propanal, methyl crotonate and ethyl propiolate. Dianion 5b reacts with alkyl halides and ethyl propiolate also at the nitrogen atom to give in the case of dihalides 6, 7, and 8 member nitrogen-containing heterocycles.

引用

页码：8867 / 8870

页数：4

共 18 条

[1] TOSYLATED LITHIUM 2-(LITHIOMETHYL)-2-PROPEN-1-OLATE - A GAMMA-ALKOXIDE ALLYL SULFONE ANION IN ORGANIC-SYNTHESIS
ALONSO, DA
NAJERA, C
SANSANO, JM
[J]. TETRAHEDRON, 1994, 50 (22) : 6603 - 6620
[2] BARLUENGA J, 1992, TETRAHEDRON LETT, V33, P7573
[3] DIRECT REGIO-SELECTIVE AND STEREO-SELECTIVE LITHIATION OF SECONDARY ALLYL AND METHYLALLYL AMINES - REACTION WITH ELECTROPHILES
BARLUENGA, J
FANANAS, FJ
FOUBELO, F
YUS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (16) : 1135 - 1136
[4] SYNTHETIC STUDIES RELATED TO PENTALENOLACTONES .2. CYCLOPENTANATION WITH 2-CHLOROMETHYL-ALLYL PHENYLSULFONE
BREUILLES, P
UGUEN, D
[J]. TETRAHEDRON LETTERS, 1988, 29 (02) : 201 - 204
[5] EISCH JJ, 1980, J ORG CHEM, V45, P4536
[6] LITHIATION OF N,N-DIMETHYLMETHALLYLAMINE
FITT, JJ
GSCHWEND, HW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) : 3349 - 3352
[7] FOUBELO F, 1989, THESIS U OVIEDO
[8] STEREOCHEMISTRY .81. MICHAEL REACTIONS OF ALLYLIC SULFONES WITH NITROOLEFINS - REGIOCHEMICAL AND STEREOCHEMICAL CONTROL
GHERA, E
BENYAAKOV, E
YECHEZKEL, T
HASSNER, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (19) : 2741 - 2744
[9] STEREOCHEMISTRY .78. A NEW DIASTEREOSELECTIVE 3+2 ANNULATION APPROACH TO 5-MEMBERED CARBOCYCLES
GHERA, E
YECHEZKEL, T
HASSNER, A
[J]. TETRAHEDRON LETTERS, 1990, 31 (25) : 3653 - 3656
[10] STEREOCHEMISTRY .84. SYNTHESIS OF NITROCYCLOPENTANES VIA A 3+2 STRATEGY
GHERA, E
YECHEZKEL, T
HASSNER, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) : 6716 - 6724

← 1 2 →