3-pyrrolidinecarboxylic acid for direct catalytic asymmetric anti-Mannich-type reactions of unmodified ketones

被引:160
作者
Zhang, Haile
Mifsud, Maria
Tanaka, Fujie
Barbas, Carlos F., III
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem & Mol Biol, La Jolla, CA 92037 USA
关键词
D O I
10.1021/ja062950b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[No abstract available]
引用
收藏
页码:9630 / 9631
页数:2
相关论文
共 28 条
[1]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[2]   5-pyrrolidin-2-yltetrazole: A new, catalytic, more soluble alternative to proline in an organocatalytic asymmetric Mannich-type reaction [J].
Cobb, AJA ;
Shaw, DM ;
Ley, SV .
SYNLETT, 2004, (03) :558-560
[3]   anti-selective SMP-catalyzed direct asymmetric Mannich-type reactions:: synthesis of functionalized amino acid derivatives [J].
Córdova, A ;
Barbas, CF .
TETRAHEDRON LETTERS, 2002, 43 (43) :7749-7752
[4]   Asymmetric synthesis of selectively protected amino sugars and derivatives by a direct organocatalytic Mannich reaction [J].
Enders, D ;
Grondal, C ;
Vrettou, M ;
Raabe, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4079-4083
[5]   Catalytic, enantioselective alkylation of α-amino esters:: The synthesis of nonnatural α-amino acid derivatives [J].
Ferraris, D ;
Young, B ;
Cox, C ;
Dudding, T ;
Drury, WJ ;
Ryzhkov, L ;
Taggi, AE ;
Lectka, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) :67-77
[6]   Diastereo- and enantioselective alkylation of α-imino esters with enol silanes catalyzed by (R)-Tol-BINAP-CuClO4•(MeCN)2 [J].
Ferraris, D ;
Young, B ;
Cox, C ;
Drury, WJ ;
Dudding, T ;
Lectka, T .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6090-6091
[7]   A general organocatalyst for direct α-functionalization of aldehydes:: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions.: Scope and mechanistic insights [J].
Franzén, J ;
Marigo, M ;
Fielenbach, D ;
Wabnitz, TC ;
Kjaersgaard, A ;
Jorgensen, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18296-18304
[8]   Enantio- and diastereoselective, stereospecific Mannich-type reactions in water [J].
Hamada, T ;
Manabe, K ;
Kodayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7768-7769
[9]   Catalytic asymmetric addition of β-ketoesters to various Imines by using chiral palladium complexes [J].
Hamashima, Y ;
Sasamoto, N ;
Hotta, D ;
Somei, H ;
Umebayashi, N ;
Sodeoka, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (10) :1525-1529
[10]   The direct, enantioselective, one-pot, three-component, Cross-Mannich reaction of aldehydes:: The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions [J].
Hayashi, Y ;
Urushima, T ;
Shoji, M ;
Uchimaru, T ;
Shiina, I .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1595-1604