Diastereoselective aldol condensation with 2-(β-ethoxycarbonyl)oxazolidine derived from norephedrine.: A chiral masked synthon of ethyl formylacetate

被引：8

作者：

García-Valverde, M ^{[1
]}

Nieto, J ^{[1
]}

Pedrosa, R ^{[1
]}

Vicente, M ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 09期

关键词：

asymmetric synthesis; chiral oxazolidines; diastereoselectivity; aldol reaction;

D O I：

10.1016/S0040-4020(99)00046-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of chiral masked synthetic equivalents of ethyl glyoxalate, derived from norephedrine, with a novel base formed by addition of tert-BuLi to tert-butyl formate. and subsequent reaction with aromatic aldehydes yields P-hydroxy esters in good yield and moderate to excellent diastereomeric excesses. Reductive transformation of the condensation products, and elimination of the chiral appendage leads to enantiomerically pure 2-aminomethyl-1,3-propanediol derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2755 / 2762

页数：8

共 10 条

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ASIAN JOURNAL OF CHEMISTRY, 1999, 11 (04) : 1334 - 1342
[2] A NEW CHIRAL GLYCINE SYNTHON - SYNTHESIS, X-RAY STRUCTURE OF (-)BULLET(2S,4R)-2-ETHOXYCARBONYL-4-PHENYL-1,3-OXAZOLIDINE AND DIASTEREOSELECTIVE NUCLEOPHILIC RING-OPENING TO (R)-ETHYL ALPHA-AMINO CARBOXYLATES
ANDRES, C
GONZALEZ, A
PEDROSA, R
PEREZENCABO, A
GARCIAGRANDA, S
SALVADO, MA
GOMEZBELTRAN, F
TETRAHEDRON LETTERS, 1992, 33 (33) : 4743 - 4746
[3] Synthesis of chiral, non-racemic 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from (1R,2S)-norephedrine.
Hitchcock, SR
Casper, DM
Nora, GP
Taylor, DC
Blackburn, JR
Bentley, JT
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U89 - U89
[4] Synthesis and characterization of cationic silsesquioxane hybrids by hydrolytic condensation of triethoxysilane derived from 2-(dimethylamino)ethyl acrylate
Mori, Hideharu
Yamada, Masato
COLLOID AND POLYMER SCIENCE, 2012, 290 (18) : 1879 - 1891
[5] Synthesis and characterization of cationic silsesquioxane hybrids by hydrolytic condensation of triethoxysilane derived from 2-(dimethylamino)ethyl acrylate
Hideharu Mori
Masato Yamada
Colloid and Polymer Science, 2012, 290 : 1879 - 1891
[6] Highly enantioselective synthesis of syn- and anti-propionate aldols without diastereoselection in the chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal derived from ethyl 2-(methylthio)propionate
Abu Hena, M
Terauchi, S
Kim, CS
Horiike, M
Kiyooka, S
TETRAHEDRON-ASYMMETRY, 1998, 9 (11) : 1883 - 1890
[7] Stereoselective reaction of α-sulfinyl carbanion derived from chiral 2-(trialkylsilyl)ethyl sulfoxides:: Evidence for a novel silicon-oxygen interaction
Nakamura, S
Takemoto, H
Ueno, Y
Toru, T
Kakumoto, T
Hagiwara, T
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02): : 469 - 474
[8] Diastereoselective Reduction of Chiral 2-(1-Alkenoyl)- and 2-(1-Alkynoyl)-1,3-Oxathiane 3-Oxides Derived from (1R)-(+)-Camphor
Ko, Kwang-Youn
Yun, Hoseop
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (07) : 2415 - 2418
[9] Synthesis of chiral 1,5-disubstituted pyrrolidinones via electrophile-induced cyclization of 2-(3-butenyl)oxazolines derived from (1R,2S)- and (1S,2R)-norephedrine
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Szakonyi, Zsolt
Sillanpaa, Reijo
D'hooghe, Matthias
De Kimpe, Norbert
Fulop, Ferenc
TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2857 - 2863
[10] SYNTHESIS AND CHARACTERIZATION OF NOVEL CHIRAL ORTHO-TELLURATED COMPLEXES DERIVED FROM [(S)-1-(DIMETHYLAMINO)ETHYL]BENZENE - CRYSTAL AND MOLECULAR-STRUCTURE OF (2-[(S)-1-(DIMETHYLAMINO)ETHYL]PHENYL)TELLURIUM TRICHLORIDE
SINGH, HB
SUDHA, N
BUTCHER, RT
INORGANIC CHEMISTRY, 1992, 31 (08) : 1431 - 1435

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