Stereoselective synthesis of α-hydroxy-β-amino acid derivatives from β-hydroxy-γ,δ-unsaturated sulfilimine

被引：13

作者：

Raghavan, Sadagopan ^{[1
]}

Mustafa, Shalk ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500 007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 20期

关键词：

N-sulfinyl benzylcarbamate; sulfoxide; N-Cbz sulfilimine; bromo carbamate; (2S; 3R)-AHDA; 3R)-AHPBA;

D O I：

10.1016/j.tetlet.2008.03.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first report on the use of N-sulfinyl benzylcarbamate for the preparation of N-Cbz sulfilimine from the corresponding sulfoxide is reported. The sulfilimine moiety is utilized as an intramolecular nucleophile for the regio- and stereoselective heterofunctionalization of an alkene to furnish a bromo carbamate which is used as a key advanced intermediate in the synthesis of representative alpha-hydroxy-beta-amino acid derivatives. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3216 / 3220

页数：5

共 50 条

[1] Stereoselective synthesis of δ-heteroaryl substituted β-hydroxy-γ,δ-unsaturated α-amino acids
Cremonesi, Giuseppe
Dalla Croce, Piero
Fontana, Francesco
La Rosa, Concetta
TETRAHEDRON-ASYMMETRY, 2006, 17 (18) : 2637 - 2641
[2] Asymmetric synthesis of β-hydroxy-α-amino acid
Makino, K
Hamada, Y
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2005, 63 (12) : 1198 - 1208
[3] Stereoselective synthesis of α-hydroxy-β-amino acids:: the chiral pool approach
Tasic, G
Matovic, R
Saicic, RN
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2004, 69 (11) : 981 - 990
[4] Asymmetric synthesis of chiral β-hydroxy-α-amino acid derivatives by organocatalytic aldol reactions of isocyanoesters with β,γ-unsaturated α-ketoesters
Lin, Ning
Deng, Yan-Qiu
Zhang, Zhen-Wei
Wang, Qian
Lu, Gui
TETRAHEDRON-ASYMMETRY, 2014, 25 (08) : 650 - 657
[5] Stereodivergent synthesis of (-)- and (+)-slaframine from γ-hydroxy-α,β-unsaturated sulfones
Carretero, JC
Arrayás, RG
SYNLETT, 1999, (01) : 49 - 52
[6] Highly stereoselective synthesis of C-(alkynyl)-pseudoglycals from δ-hydroxy-α,β-unsaturated aldehydes
Yadav, J. S.
Raju, A. Krishnam
Sunitha, V.
TETRAHEDRON LETTERS, 2006, 47 (30) : 5269 - 5272
[7] Synthesis of (+)-5α-Hydroxy-β-selinene and (-)-5β-hydroxy-β-selinene
Xiong, ZM
Zhou, G
Chen, YG
Li, YL
CHINESE CHEMICAL LETTERS, 1998, 9 (07) : 629 - 630
[8] Stereoselective synthesis of chiral γ-hydroxy-β-methyl methylcarbinols
Chakraborty, TK
Thippeswamy, D
Jayaprakash, S
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1998, 75 (10-12) : 741 - 745
[9] Synthesis of (+)-5α-Hydroxy-β-selinene and (-)-5β-Hydroxy-β-selinene
Zhao Ming XIONG
Gang ZHOU
Yong Gang CHEN and Yu Lin LI(National Laboratory of Applied organic Chemistry and Institute of Organic Chemistry
Chinese Chemical Letters, 1998, (07) : 629 - 630
[10] Novel synthesis of α-trifluoromethylated α-amino acid derivatives from γ-hydroxy-α-fluoro-α-trifluoromethyl carboxamides
Ogu, K
Matsumoto, S
Akazome, M
Ogura, K
ORGANIC LETTERS, 2005, 7 (04) : 589 - 592

← 1 2 3 4 5 →