Stereocontrolled synthesis of all four stereoisomers of fully protected 2-amino-3-hydroxypentanoic acid from imines derived from D-glyceraldehyde

被引：12

作者：

Badorrey, R ^{[1
]}

Cativiela, C ^{[1
]}

Díaz-de-Villegas, MD ^{[1
]}

Gálvez, JA ^{[1
]}

机构：

[1] Univ Zaragoza, Fac Ciencias, Dept Quim Organ, Inst Ciencia Mat Aragon,CSIC, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON | 1999年 / 55卷 / 49期

关键词：

addition reactions; amino acids and derivatives; asymmetric synthesis; Grignard reagents; imines;

D O I：

10.1016/S0040-4020(99)00880-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Benzylimines derived from conveniently protected (R)-glyceraldehyde underwent diastereoselective phenylmagnesium bromide addition to afford the corresponding aminodiols, whose absolute configuration at the newly formed stereogenic carbon depends on the O-protecting group. These compounds can be easily transformed into optically pure N-tert-butoxycarbonyl- 1-phenyl-2,3-epoxy-1-propylamines, which are key intermediates in the synthesis of 2-tert-butoxycarbonylamino-3-acetyloxypentanoates of erythro and three configuration. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14145 / 14160

页数：16

共 50 条

[1] STEREOCONTROLLED ADDITION OF 2-LITHIOTHIAZOLE TO THE NITRONE DERIVED FROM D-GLYCERALDEHYDE ACETONIDE - A REVISION AND EXTENSION
DONDONI, A
FRANCO, S
MERCHAN, FL
MERINO, P
TEJERO, T
TETRAHEDRON LETTERS, 1993, 34 (34) : 5475 - 5478
[2] STEREOCONTROLLED SYNTHESIS OF D-PENTITOLS, 2-AMINO-2-DEOXY-D-PENTITOLS, AND 2-DEOXY-D-PENTITOLS FROM D-GLYCERALDEHYDE ACETONIDE
MINAMI, N
KO, SS
KISHI, Y
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) : 1109 - 1111
[3] STEREOCONTROLLED SYNTHESIS OF ALL 4 STEREOISOMERS OF VERRUCARINOLACTONE FROM (R)-2,3-O-ISOPROPYLIDENE-GLYCERALDEHYDE
MULZER, J
SALIMI, N
LIEBIGS ANNALEN DER CHEMIE, 1986, (07): : 1172 - 1178
[4] DIASTEREOSELECTIVE STRECKER REACTION OF IMINES DERIVED FROM D-GLYCERALDEHYDE - A NEW ROUTE TO BETA-HYDROXY-ALPHA-AMINO ACIDS
CATIVIELA, C
DIAZDEVILLEGAS, MD
GALVEZ, JA
TETRAHEDRON LETTERS, 1995, 36 (16) : 2859 - 2860
[5] Lewis acid-promoted synthesis and reactivity of β-O-benzylhydroxylamino imides derived from D-glyceraldehyde
Cardillo, G
Gentilucci, L
De Matteis, V
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17): : 5957 - 5962
[6] Chiral Iminoesters Derived from D-Glyceraldehyde in [3+2] Cycloaddition Reactions. Asymmetric Synthesis of a Key Intermediate in the Synthesis of Neuramidinase Inhibitors
Galvez, Jose A.
Diaz-de-Villegas, Maria D.
Alias, Miriam
Badorrey, Ramon
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (22): : 11404 - 11413
[7] Study of the reactions between vinylmagnesium bromide and imines derived from (R)-glyceraldehyde -: The key step in the stereodivergent synthesis of conveniently protected, enantiopure syn- and anti-2-amino-1,3,4-butanetriol derivatives
Badorrey, R
Cativiela, C
Díaz-De-Villegas, MD
Díez, R
Gálvez, JA
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) : 2268 - 2275
[8] Stereocontrolled synthesis of syn and anti N-protected 3-amino-2-hydroxy alkanoic esters from aminoalkyl epoxides
Pegorier, L
Haddad, M
Larcheveque, M
SYNLETT, 1996, (06) : 585 - &
[9] Synthesis and antifungal evaluation of imines derived from 3-Amino-2-isopropyl-3H-quinazolin-4-one
Karakaya, Idris
Karabuga, Semistan
Ulukanli, Zeynep
Ulukanli, Sabri
ORGANIC COMMUNICATIONS, 2013, 6 (04) : 139 - 147
[10] Electrophilic sulfenylation in a stereocontrolled synthesis of protected (2R,3R)-3-mercaptoaspartic acid from L-aspartic acid
Shibata, N.
Baldwin, J. E.
Jacobs, A.
Wood, M. E.
Tetrahedron, 52 (39):

← 1 2 3 4 5 →