γ-butyltelluro-2-butanol:: a route to reactive 1,4-dianion intermediates

被引：27

作者：

Princival, JL

de Barros, SMG

Comasseto, JV

Dos Santos, AA

机构：

[1] Univ Sao Paulo, IQ, BR-05508900 Sao Paulo, Brazil

[2] Univ Fed Pernambuco, DQF, BR-50740540 Recife, PE, Brazil

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 26期

基金：

巴西圣保罗研究基金会;

关键词：

tellurium/lithium exchange; 1,4-dianion and diols;

D O I：

10.1016/j.tetlet.2005.05.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

gamma-Butyltelluro-2-butanol was reacted with 2 equiv of n-butyllithium. Both tellurium/lithium exchange and the proton abstraction reactions took place in a single step and the lithium dianion intermediate efficiently reacted with aldehydes and ketones, producing the corresponding diols. (c) 2005 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4423 / 4425

页数：3

相关论文

共 18 条

[1] A GENERAL DIASTEREOSELECTIVE SYNTHESIS OF SPIROACETALS RELATED TO THOSE IN IONOPHORES VIA THE REACTION OF LACTONES WITH CERIUM(III) GAMMA-CERIOALKOXIDE - MAD REVERSES THE DIASTEREOSELECTIVITY OF THE ADDITION OF METHYLMETALLICS TO A BETA-KETO ETHER [J].

AHN, Y ;

COHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3142-3150

[2] Functionalized organolithium compounds in total synthesis [J].

Chinchilla, R ;

Nájera, C ;

Yus, M .

TETRAHEDRON, 2005, 61 (13) :3139-3176

[3] ORGANIC TELLURIUM AND SELENIUM CHEMISTRY - REDUCTION OF TELLURIDES, SELENIDES, AND SELENOACETALS WITH TRIPHENYLTIN HYDRIDE [J].

CLIVE, DLJ ;

CHITTATTU, GJ ;

FARINA, V ;

KIEL, WA ;

MENCHEN, SM ;

RUSSELL, CG ;

SINGH, A ;

WONG, CK ;

CURTIS, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4438-4447

[4] Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers [J].

Cohen, T ;

Tong, SJ .

TETRAHEDRON, 1997, 53 (28) :9487-9496

[5] THE USE OF AMINOIMINOMETHANESULFINIC ACID (THIOUREA DIOXIDE) UNDER PHASE-TRANSFER CONDITIONS FOR GENERATING ORGANOCHALCOGENATE ANIONS - SYNTHESIS OF SULFIDES, SELENIDES AND TELLURIDES [J].

COMASSETO, JV ;

LANG, ES ;

FERREIRA, JTB ;

SIMONELLI, F ;

CORREIA, VR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 334 (03) :329-340

[6]

Comasseto JV, 2000, ALDRICHIM ACTA, V33, P66

[7] SYNTHESIS OF VINYLIC TELLURIDES [J].

DABDOUB, MJ ;

DABDOUB, VB ;

COMASSETO, JV ;

PETRAGNANI, N .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 308 (02) :211-222

[8] Synthesis and bioassay of 4-ipomeanol analogs as potential chemopreventive agents against 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced tumorigenicity in A/J mice [J].

Desai, D ;

Chang, LH ;

Amin, S .

CANCER LETTERS, 1996, 108 (02) :263-270

[9] IPOMEANOL ANALOGS AS CHEMOPREVENTIVE AGENTS - EFFECT ON THE IN-VITRO METABOLISM OF 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANONE (NNK) [J].

DESAI, D ;

NUNES, M ;

CHANG, L ;

LIN, JM ;

JIAO, D ;

AMIN, S .

CANCER LETTERS, 1995, 97 (02) :155-162

[10] β-Butyltellanyl carbonyl compounds:: A useful source of masked metal homoenolates [J].

Dos Santos, AA ;

Comasseto, JV .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2005, 16 (3B) :511-513