Chiral diphenylprolinol TES ether promoted conjugate addition-aldol-dehydration reactions between α,β-unsaturated aldehydes and 2-N-protected amino benzaldehydes

被引:122
作者
Li, Hao [1 ]
Wang, Jian [1 ]
Xie, Hexin [1 ]
Zu, Liansuo [1 ]
Jiang, Wei [1 ]
Duesler, Eileen N. [1 ]
Wang, Wei [1 ]
机构
[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA
关键词
D O I
10.1021/ol062877u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A conjugate addition-aldol-dehydration reaction of alpha,beta-unsaturated aldehydes with 2-N-protected amino benzaldehydes has been developed. The process is promoted by (S)-diphenylprolinol TES ether to afford synthetically useful 1,2-dihydroquinolines in high enantioselectivities with good yields.
引用
收藏
页码:965 / 968
页数:4
相关论文
共 53 条
[42]   Enantioselective thiourea-catalyzed acyl-Mannich reactions of isoquinolines [J].
Taylor, MS ;
Tokunaga, N ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (41) :6700-6704
[43]   Asymmetric catalysis by chiral hydrogen-bond donors [J].
Taylor, MS ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1520-1543
[44]   Domino reactions in the synthesis of heterocyclic natural products and analogs [J].
Tietze, LF ;
Rackelmann, N .
PURE AND APPLIED CHEMISTRY, 2004, 76 (11) :1967-1983
[45]   Domino reactions in organic synthesis [J].
Tietze, LF .
CHEMICAL REVIEWS, 1996, 96 (01) :115-136
[46]   Highly enantioselective iridium-catalyzed hydrogenation of heteroaromatic compounds, quinolines [J].
Wang, WB ;
Lu, SM ;
Yang, PY ;
Han, XW ;
Zhou, YG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (35) :10536-10537
[47]   Enantioselective organocatalytic tandem Michael-aldol reactions: One-pot synthesis of chiral thiochromenes [J].
Wang, Wei ;
Li, Hao ;
Wang, Jian ;
Zu, Liansuo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (32) :10354-10355
[48]   Dual-function cinchona alkaloid catalysis: Catalytic asymmetric tandem conjugate addition-protonation for the direct creation of nonadjacent stereocenters [J].
Wang, Y ;
Liu, XF ;
Deng, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3928-3930
[49]   MARTINELLINE AND MARTINELLIC ACID, NOVEL G-PROTEIN LINKED RECEPTOR ANTAGONISTS FROM THE TROPICAL PLANT MARTINELLA-IQUITOSENSIS (BIGNONIACEAE) [J].
WITHERUP, KM ;
RANSOM, RW ;
GRAHAM, AC ;
BERNARD, AM ;
SALVATORE, MJ ;
LUMMA, WC ;
ANDERSON, PS ;
PITZENBERGER, SM ;
VARGA, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (25) :6682-6685
[50]   A catalytic enantioselective aza-Michael reaction:: Novel protocols for asymmetric synthesis of β-amino carbonyl compounds [J].
Xu, LW ;
Xia, CG .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (04) :633-639