Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity

被引:130
作者
Akiyama, T [1 ]
Tamura, Y [1 ]
Itoh, J [1 ]
Morita, H [1 ]
Fuchibe, K [1 ]
机构
[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
关键词
asymmetric synthesis; chiral Bronsted acid; aza-Diels-Alder reaction; Danishefsky's diene;
D O I
10.1055/s-2005-922773
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Danishefsky's diene and aldimine underwent aza Diels-Alder reaction under the influence of chiral phosphoric;acid derived from (R)-BINOL as a chiral Bronsted acid to afford piperidinone derivatives in good to high enantioselectivity. Addition of CH,CO,H improved both reactivity and enantioselectivity.
引用
收藏
页码:141 / 143
页数:3
相关论文
共 37 条
[1]
Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].
Akiyama, T ;
Saitoh, Y ;
Morita, H ;
Fuchibe, K .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526
[2]
Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].
Akiyama, T ;
Morita, H ;
Itoh, J ;
Fuchibe, K .
ORGANIC LETTERS, 2005, 7 (13) :2583-2585
[3]
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
[4]
Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
TETRAHEDRON LETTERS, 1999, 40 (44) :7831-7834
[5]
Enantioselective organocatalytic α-fluorination of aldehydes [J].
Beeson, TD ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828
[6]
USEFUL DIENE FOR DIELS-ALDER REACTION [J].
DANISHEFSKY, S ;
KITAHARA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7807-7808
[7]
Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation:: A one-step synthesis of (S)-(+)-Dihydrokawain [J].
Du, HF ;
Zhao, DB ;
Ding, KL .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) :5964-5970
[8]
Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst [J].
Huang, Y ;
Unni, AK ;
Thadani, AN ;
Rawal, VH .
NATURE, 2003, 424 (6945) :146-146
[9]
MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST [J].
HUBERT, AJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :1984-&
[10]
A NEW CHIRAL BLA PROMOTER FOR ASYMMETRIC AZA-DIELS-ALDER AND ALDOL-TYPE REACTIONS OF IMINES [J].
ISHIHARA, K ;
MIYATA, M ;
HATTORI, K ;
TADA, T ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10520-10524