Catalytic enantioselective aldol additions of α-isothiocyanato imides to α-ketoesters

被引：39

作者：

Vecchione, Matthew K. ^{[1
]}

Li, Le ^{[1
]}

Seidel, Daniel ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 25期

关键词：

AMINO ACID-DERIVATIVES; QUATERNARY AMMONIUM-SALTS; ASYMMETRIC-SYNTHESIS; CINCHONA ALKALOIDS; NONADJACENT STEREOCENTERS; CONJUGATE ADDITION; EFFICIENT APPROACH; CYCLIC-PEPTIDES; BOND DONORS; SCHIFF-BASE;

D O I：

10.1039/c0cc00556h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A readily available bifunctional thiourea catalyst promotes aldol additions of alpha-isothiocyanato imides to alpha-ketoesters under mild reaction conditions to form beta-hydroxy-alpha-amino acid derivatives with high levels of enantioselectivity.

引用

页码：4604 / 4606

页数：3

共 72 条

[41] The advent and development of organocatalysis [J].

MacMillan, David W. C. .

NATURE, 2008, 455 (7211) :304-308

[42] Lobocyclamide B from Lyngbya confervoides.: Configuration and asymmetric synthesis of β-hydroxy-α-amino acids by (-)-sparteine-mediated aldol addition [J].

MacMillan, JB ;

Molinski, TF .

ORGANIC LETTERS, 2002, 4 (11) :1883-1886

[43] Stereoselective synthesis of anti-β-hydroxy-α-amino acids through dynamic kinetic resolution [J].

Makino, K ;

Goto, T ;

Hiroki, Y ;

Hamada, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :882-884

[44] Cupreines and cupreidines: An emerging class of bifunctional cinchona organocatalysts [J].

Marcelli, Tommaso ;

van Maarseveen, Jan H. ;

Hiemstra, Henk .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7496-7504

[45] Catalytic asymmetric synthesis of α-amino acids [J].

Najera, Carmen ;

Sansano, Jose M. .

CHEMICAL REVIEWS, 2007, 107 (11) :4584-4671

[46]

Nicolaou KC, 1999, ANGEW CHEM INT EDIT, V38, P2096, DOI 10.1002/(SICI)1521-3773(19990802)38:15<2096::AID-ANIE2096>3.0.CO

[47]

2-F

[48] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673

[49] Development of highly diastereo- and enantioselective direct asymmetric aldol reaction of a glycinate Schiff base with aldehydes catalyzed by chiral quaternary ammonium salts [J].

Ooi, T ;

Kameda, M ;

Taniguchi, M ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9685-9694

[50]

Ooi T, 2002, ANGEW CHEM INT EDIT, V41, P4542, DOI 10.1002/1521-3773(20021202)41:23<4542::AID-ANIE4542>3.0.CO

← 1 2 3 4 5 6 7 8 →