Asymmetric allylic alkylation catalyzed by palladium complexes with atropisomeric quinazolinone phosphine ligands

被引:51
作者
Dai, XD [1 ]
Virgil, S [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
3-aryl-4(3H)-quinazolinone; atropisomeric; phosphine ligands; asymmetric allylic alkylation;
D O I
10.1016/S0040-4039(98)02599-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric inductions up to 52% ee and 87% ee have been achieved with palladium catalyzed allylic alkylation reactions using a new class of atropisomeric monodentate ((R)-1b) and chelate (2) quinazolinone phosphine ligands, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1245 / 1248
页数:4
相关论文
共 13 条
[1]   A NEW CLASS OF CHIRAL PHOSPHORUS CATALYST FOR ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS [J].
BRENCHLEY, G ;
MERIFIELD, E ;
WILLS, M ;
FEDOULOFF, M .
TETRAHEDRON LETTERS, 1994, 35 (17) :2791-2794
[2]   Syntheses of novel chiral monophosphines, 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes, and their application in highly enantioselective Pd-catalyzed allylic alkylations [J].
Chen, ZG ;
Jiang, QZ ;
Zhu, GX ;
Xiao, DM ;
Cao, P ;
Guo, C ;
Zhang, XM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4521-4523
[3]   Synthesis and resolution of quinazolinone atropisomeric phosphine ligands [J].
Dai, XD ;
Wong, A ;
Virgil, SC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2597-2600
[4]   ASYMMETRIC PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION USING PHOSPHORUS-CONTAINING OXAZOLINE LIGANDS [J].
DAWSON, GJ ;
FROST, CG ;
WILLIAMS, JMJ .
TETRAHEDRON LETTERS, 1993, 34 (19) :3149-3150
[5]   New monodentate chiral phosphine 2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1]nonane(9-PBN): Application to asymmetric allylic substitution reaction [J].
Hamada, Y ;
Seto, N ;
Ohmori, H ;
Hatano, K .
TETRAHEDRON LETTERS, 1996, 37 (42) :7565-7568
[6]   FUNCTIONALIZATION OF 2-METHYL-3-ORTHO-TOLYL-4(3H)-QUINAZOLINONE AND RELATED-COMPOUNDS THROUGH CARBANION REACTIONS AT THE 2-METHYL GROUP [J].
RATHMAN, TL ;
SLEEVI, MC ;
KRAFFT, ME ;
WOLFE, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (11) :2169-2176
[7]   Lithiation of 2-alkyl-3-amino- and 2-alkyl-3-(methylamino)-4(3H)-quinazolinones [J].
Smith, K ;
ElHiti, GA ;
AbdelMegeed, MF ;
Abdo, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :656-661
[8]   PHOSPHINOARYLOXAZOLINES AND PHOSPHINOALKYLOXAZOLINES AS NEW CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS - VERY HIGH ENANTIOSELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTIONS [J].
SPRINZ, J ;
HELMCHEN, G .
TETRAHEDRON LETTERS, 1993, 34 (11) :1769-1772
[9]   Asymmetric transition metal-catalyzed allylic alkylations [J].
Trost, BM ;
VanVranken, DL .
CHEMICAL REVIEWS, 1996, 96 (01) :395-422
[10]   ASYMMETRIC-SYNTHESIS OF ALLYLIC SULFONES - USEFUL ASYMMETRIC BUILDING-BLOCKS [J].
TROST, BM ;
ORGAN, MG ;
ODOHERTY, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (38) :9662-9670