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

[41] SYNTHESIS OF OPTICALLY-ACTIVE NATURAL CAROTENOIDS AND STRUCTURALLY RELATED-COMPOUNDS .9. SYNTHESIS OF (3R)-HYDROXYECHINENONE, (3R,3'R)-ADONIXANTHIN AND (3R,3'S)-ADONIXANTHIN, (3R)-ADONIRUBIN, THEIR OPTICAL-ANTIPODES AND RELATED-COMPOUNDS
BERNHARD, K
ENGLERT, G
MAYER, H
MULLER, RK
RUTTIMANN, A
VECCHI, M
WIDMER, E
ZELL, R
HELVETICA CHIMICA ACTA, 1981, 64 (07) : 2469 - 2484
[42] First asymmetric synthesis of (2R,3R)-3-amino-1-benzyl-2-methylpyrrolidine via a highly diastereoselective reductive alkylation
Huang, PQ
Wang, SL
Zheng, H
Fei, XS
TETRAHEDRON LETTERS, 1997, 38 (02) : 271 - 272
[43] ORGANOBORON COMPOUNDS IN ORGANIC-SYNTHESIS .3. MECHANISM OF ASYMMETRIC REDUCTION OF DIALKYL KETONES WITH (R,R)-2,5-DIMETHYLBOROLANE
MASAMUNE, S
KENNEDY, RM
PETERSEN, JS
HOUK, KN
WU, Y
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) : 7404 - 7405
[44] Synthesis of (1R,2R)-DPEN-derived triazolium salts and their application in asymmetric intramolecular Stetter reactions
Jia, Min-Qiang
Li, Yi
Rong, Zi-Qiang
You, Shu-Li
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) : 2072 - 2074
[45] Synthesis of Chiral Polyamides Containing an (R,R)-1,2-Diphenylethylenediamine Monosulfonamide Structure and Their Application to Asymmetric Transfer Hydrogenation Catalysis
Itsuno, Shinichi
Takahashi, Shotaro
CHEMCATCHEM, 2017, 9 (03) : 385 - 388
[46] Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones
Davies, Stephen G.
Lee, James A.
Roberts, Paul M.
Thomson, James E.
Yin, Jingda
ORGANIC LETTERS, 2012, 14 (01) : 218 - 221
[47] Hydroxynitrile lyase from Passiflora edulis: Purification, characteristics and application in asymmetric synthesis of (R)-mandelonitrile
Ueatrongchit, Techawaree
Tamura, Ken'ichirou
Ohmiya, Tohru
H-Kittikun, Aran
Asano, Yasuhisa
ENZYME AND MICROBIAL TECHNOLOGY, 2010, 46 (06) : 456 - 465
[48] Synthesis of (+)-ginnol, a type Rlong-CH(OH)-R′long alcohol, by an asymmetric β,γ-unsaturated ester→γ-butyrolactone conversion
Berkenbusch, T
Bruckner, R
TETRAHEDRON, 1998, 54 (38) : 11471 - 11480
[49] Pd-catalyzed asymmetric allylic alkylation with nitromethane using a chiral diaminophosphine oxide:: (S,RP)-Ph-DIAPHOX.: Enantioselective synthesis of (R)-preclamol and (R)-baclofen
Nemoto, Tetsuhiro
Jin, Long
Nakamura, Hiroshi
Hamada, Yasumasa
TETRAHEDRON LETTERS, 2006, 47 (37) : 6577 - 6581
[50] Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3+2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(-)-Puraquinonic Acid
Oga, Miho
Takamatsu, Yusei
Ogura, Akihiro
Takao, Ken-ichi
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8788 - 8795

← 1 2 3 4 5 →