Asymmetric synthesis of quaternary α-amino acids using D-ribonolactone acetonide as chiral auxiliary

被引：14

作者：

Moreno-Mañas, M ^{[1
]}

Trepat, E ^{[1
]}

Sebastián, RM ^{[1
]}

Vallribera, A ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 21期

关键词：

D O I：

10.1016/S0957-4166(99)00457-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We describe a new simple methodology to prepare enantiopure alpha,alpha-dialkylglycines based on the use of commercially available D-ribonolactone as a chiral auxiliary. Enantiopure alpha-methyl and alpha-butyl series are prepared through diastereoselective alkylation and subsequent Schmidt rearrangement of alpha,alpha-dialkylacetoacetates of D-ribonolactone acetonide. Absolute configuration was assigned through preparation of enantiopure 4,4-disubstituted 3-methyl-2-pyrazolin-5-ones. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4211 / 4224

页数：14

共 50 条

[1] TOTAL SYNTHESIS OF (+)-ELDANOLIDE FROM D-RIBONOLACTONE
ORTUNO, RM
MERCE, R
FONT, J
TETRAHEDRON LETTERS, 1986, 27 (22) : 2519 - 2522
[2] SYNTHESIS OF (-)-GALANTINIC ACID FROM D-RIBONOLACTONE
IKOTA, N
HETEROCYCLES, 1991, 32 (03) : 521 - 528
[3] D-RIBONOLACTONE IN ORGANIC-SYNTHESIS - A REVIEW
BHAT, KL
CHEN, SY
JOULLIE, MM
HETEROCYCLES, 1985, 23 (03) : 691 - 729
[4] A CHIRAL SYNTHESIS OF (+)-LINEATIN, THE AGGREGATION PHEROMONE OF TRYPODENDRON LINEATUM (OLIVIER), FROM D-RIBONOLACTONE
KANDIL, AA
SLESSOR, KN
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26): : 5649 - 5655
[5] An Efficient Total Synthesis of (+)-Varitriol from D-Ribonolactone
Karlubikova, Ol'ga
Palik, Miroslav
Lasikova, Angelika
Gracza, Tibor
SYNTHESIS-STUTTGART, 2010, (20): : 3449 - 3452
[6] Synthesis of α-substituted β-amino acids using pseudoephedrine as a chiral auxiliary
Nagula, G
Huber, VJ
Lum, C
Goodman, BA
ORGANIC LETTERS, 2000, 2 (22) : 3527 - 3529
[7] ASYMMETRIC SYNTHESIS——ENANTIOSELECTIVE SYNTHESIS OF (R)-α-AMINO ACIDS USING L-ISOLEUCINE AS CHIRAL AUXILIARY REAGENT
蒋耀忠
U.SCHLLKOPF
U.GROTH
Science China Chemistry, 1984, (06) : 566 - 571
[8] ASYMMETRIC SYNTHESIS——ENANTIOSELECTIVE SYNTHESIS OF (R)-α-AMINO ACIDS USING L-ISOLEUCINE AS CHIRAL AUXILIARY REAGENT
蒋耀忠
U.SCHLLKOPF
U.GROTH
Science in China,SerB., 1984, Ser.B.1984 (06) : 566 - 571
[9] A NEW SYNTHESIS OF D-RIBONOLACTONE FROM D-RIBOSE BY PYRIDINIUM CHLOROCHROMATE OXIDATION
LIU, DS
CAPERELLI, CA
SYNTHESIS-STUTTGART, 1991, (11): : 933 - 934
[10] SYNTHESIS OF SUGARS FROM D-RIBONOLACTONE .2. AN ALTERNATIVE SYNTHESIS OF D-ERYTHROSE
SHAH, RH
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (01) : 139 - 146

← 1 2 3 4 5 →