Asymmetric α-alkylation of α,β-unsaturated esters.: Application to the synthesis of (R)-lavandulol, (R)-sesquilavandulol and related trifluoromethyl compounds

被引：0

作者：

Faure, S ^{[1
]}

Piva, O ^{[1
]}

机构：

[1] Univ Reims, CNRS, UMR 6519, UFR Sci, F-51687 Reims, France

来源：

SYNLETT | 1998年 / 12期

关键词：

lavandulol; sesquilavandulol; asymmetric alkylation; diacetone D-glucose; trifluoromethyl compounds;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective alpha-alkylation/deconjugation of esters of diacetone D-glucose has been performed and applied to the syntheses of (R)-lavandulol, (R)-sesquilavandulol with de up to 74%. The same reaction performed with trifluoromethyl derivatives was also achieved but without significant diastereoselectivity.

引用

页码：1414 / 1416

页数：3

共 50 条

[21] Synthesis of novel derivatives of (R)-cysteine and their application in asymmetric reduction of prochiral ketones
Hui, W
Pei, WW
Ye, WP
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2005, 21 (05) : 536 - 539
[22] Synthesis of Novel Derivatives of (R)-Cysteine and Their Application in Asymmetric Reduction of Prochiral Ketones
WANG Hui
ChemicalResearchinChineseUniversities, 2005, (05) : 536 - 539
[23] A 2-STEP ASYMMETRIC-SYNTHESIS OF (R)-MONOARYL EPOXIDES USING A CHIRAL OXATHIANE AS A RECOVERABLE REAGENT - APPLICATION TO THE PREPARATION OF (R)-BETA-ADRENERGIC COMPOUNDS
SOLLADIECAVALLO, A
DIEPVOHUULE, A
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3494 - 3498
[24] Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4:: enantioselective synthesis of (R)-baclofen and (R)-rolipram
Paraskar, AS
Sudalai, A
TETRAHEDRON, 2006, 62 (20) : 4907 - 4916
[25] SYNTHESIS OF R2SNBR2-TYPE COMPOUNDS, CATALYZED BY CROWN-ESTERS
KOTLYAR, SA
DIMITRISHCHUK, GV
SAVRANSKAYA, RL
LUKYANENKO, NG
ZHURNAL OBSHCHEI KHIMII, 1988, 58 (06): : 1443 - 1444
[26] PREPARATION OF (R)-(E)-4-HYDROXY-2-UNSATURATED AND (S)-(E)-4-HYDROXY-2-UNSATURATED ACIDS BY ASYMMETRIC HYDROLYSIS OF THEIR RACEMIC ESTERS
ALLEVI, P
ANASTASIA, M
CIUFFREDA, P
SANVITO, AM
TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1397 - 1400
[27] STEREOSELECTIVE ALPHA-ALKYLATION OF ALPHA,BETA-UNSATURATED ESTERS UTILIZING CONJUGATE ADDITION OF NITROGEN NUCLEOPHILES (R2NLI)
UYEHARA, T
ASAO, N
YAMAMOTO, Y
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) : 1410 - 1411
[28] SYNTHESIS AND CHARACTERIZATION OF THE MONOMERIC PHOSPHINOGALLANES BU(T)(2)GAPR'R'' (R', R'' = BULKY ARYL OR SILYL GROUPS) AND RELATED-COMPOUNDS
PETRIE, MA
POWER, PP
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (11): : 1737 - 1745
[29] SYNTHESIS OF OPTICALLY-ACTIVE NATURAL CAROTENOIDS AND STRUCTURALLY RELATED-COMPOUNDS .4. SYNTHESIS OF (3R,3'R,6'R)-LUTEIN
MAYER, H
RUTTIMANN, A
HELVETICA CHIMICA ACTA, 1980, 63 (06) : 1451 - 1455
[30] HClO4•SiO2-mediated Improved Isomerization of Glycidic Esters to α-Hydroxy-β,γ-unsaturated Esters: Application in the Formal Synthesis of (R)-Baclofen and β-Phenyl GABA Analogues
Basak, Ranjan
Dharuman, Suresh
Reddy, Y. Suman
Doddi, Venkata Ramana
Vankar, Yashwant D.
CHEMISTRY LETTERS, 2012, 41 (03) : 325 - 327

← 1 2 3 4 5 →