Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes

被引：35

作者：

Chen, Xiaohong ^{[1
]}

Zhu, Yin ^{[1
]}

Qiao, Zhen ^{[1
]}

Xie, Mingsheng ^{[1
]}

Lin, Lili ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 33期

基金：

中国国家自然科学基金;

关键词：

aldol reaction; amino acids; asymmetric catalysis; nickel; nitrogen oxides; ENANTIOSELECTIVE MICHAEL ADDITIONS; INTRAMOLECULAR 4+2 CYCLOADDITIONS; DIELS-ALDER REACTION; CONJUGATE ADDITION; LEWIS-ACID; 1,3-DICARBONYL COMPOUNDS; CONVENIENT SYNTHESIS; NICKEL; COMPLEXES; ESTERS;

D O I：

10.1002/chem.201000284

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An easily available and efficient chiral N,N'-dioxide-nickel(II) complex catalyst has been developed for the direct catalytic asymmetric aldol reaction of alpha-isothiocyanato imide with aldehydes which produces the products in morderate to high yields (up to 98%) with excellent diastereo- (up to > 99: 1 d.r.) and enantio- selectivities (up to > 99% ee). A variety of aromatic, heteroaromatic, alpha,beta-unsaturated, and aliphatic aldehydes were found to be suitable substrates in the presence of 2.5 mol% L-proline-derived N,N'-dioxide L5-nickel(II) complex. This process was air- tolerant and easily manipulated with available reagents. Based on experimental investigations, a possible transition state has been proposed to explain the origin of reactivity and asymmetric inductivity.

引用

页码：10124 / 10129

页数：6

共 107 条

[81] Syntheses of four unusual amino acids, constituents of cyclomarin A [J].

Sugiyama, H ;

Shioiri, T ;

Yokokawa, F .

TETRAHEDRON LETTERS, 2002, 43 (19) :3489-3492

[82] Highly Enantioselective Aza-Henry Reaction of Ketoimines Catalyzed by Chiral N,N′-Dioxide-Copper(I) Complexes [J].

Tan, Cheng ;

Liu, Xiaohua ;

Wang, Liwei ;

Wang, Jun ;

Feng, Xiaoming .

ORGANIC LETTERS, 2008, 10 (22) :5305-5308

[83]

Wang L., 2008, ANGEW CHEM, V120, P8798

[84] Asymmetric Intramolecular Oxa-Michael Addition of Activated α,β-Unsaturated Ketones Catalyzed by a Chiral N,N′-Dioxide Nickel(II) Complex: Highly Enantioselective Synthesis of Flavanones [J].

Wang, Lijia ;

Liu, Xiaohua ;

Dong, Zhenhua ;

Fu, Xuan ;

Feng, Xiaoming .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (45) :8670-8673

[85] Transition metal catalyzed cycloadditions: An intramolecular [4+4] cycloaddition strategy for the efficient synthesis of dicyclopenta[a,d]cyclooctene 5-8-5 ring systems [J].

Wender, PA ;

Nuss, JM ;

Smith, DB ;

SuarezSobrino, A ;

Vagberg, J ;

Decosta, D ;

Bordner, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :4908-4909

[86] INTRAMOLECULAR NICKEL CATALYZED CYCLOADDITIONS OF BIS-DIENES .3. APPROACHES TO THE TAXANE SKELETON [J].

WENDER, PA ;

SNAPPER, ML .

TETRAHEDRON LETTERS, 1987, 28 (20) :2221-2224

[87] NICKEL-CATALYZED INTRAMOLECULAR [4 + 4] CYCLOADDITIONS - A NEW METHOD FOR THE SYNTHESIS OF POLYCYCLES CONTAINING 8-MEMBERED RINGS [J].

WENDER, PA ;

IHLE, NC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4678-4679

[88]

WENDER PA, 1991, SYNTHESIS-STUTTGART, P1089

[89] NICKEL-CATALYZED INTRAMOLECULAR [4 + 4] CYCLO-ADDITIONS .4. ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-ASTERISCANOLIDE [J].

WENDER, PA ;

IHLE, NC ;

CORREIA, CRD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5904-5906

[90] TRANSITION-METAL-CATALYZED INTRAMOLECULAR [4+2] CYCLOADDITIONS - INITIAL STUDIES ON STEREOCHEMISTRY AND ON STEROID AND VITAMIN-D ANALOG SYNTHESES [J].

WENDER, PA ;

SMITH, TE .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :2962-2963

← 2 3 4 5 6 7 8 9 10 11 →