CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD REAGENTS TO CYCLIC ENONES USING C1-1,1′-BISISOQUINOLINE-BASED CHIRAL LIGANDS

被引：4

作者：

Qi, Gao ^{[1
]}

Judeh, Zaher M. A. ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Chem & Biomed Engn, Singapore 637459, Singapore

来源：

SYNTHETIC COMMUNICATIONS | 2012年 / 42卷 / 11期

关键词：

Asymmetric catalysis; C-1-1,1 '-bisisoquinoline; cyclic enones; enantioselective conjugate addition; N-ACYL; 1,4-ADDITION; DIETHYLZINC;

D O I：

10.1080/00397911.2010.541969

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New highly constrained chiral C-1-1,1'-bisisoquinoline ligands were examined in the enantioselective conjugate addition of Grignard reagents to cyclohexenone and cyclopentenone. The desired 1,4-adducts were obtained in excellent yield and moderate enantiomeric excess (up to 35%).

引用

页码：1585 / 1592

页数：8

共 33 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[2] Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc [J].

Alexakis, A ;

Polet, D ;

Rosset, S ;

March, S .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5660-5667

[3] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

FRUTOS, J ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2427-2430

[4] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands [J].

Alexakis, A ;

Burton, J ;

Vastra, J ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :3987-3990

[5] New N-acyl, N-alkyl, and N-bridged derivatives of rac-6,6′,7,7′-tetramethoxy-1,1′,2,2′,3,3′,4,4′-octahydro-1,1′-bisisoquinoline [J].

Busato, S ;

Craig, DC ;

Judeh, ZMA ;

Read, RW .

TETRAHEDRON, 2003, 59 (04) :461-472

[6] Structural studies of N-acyl 1,1′-bis(1,2,3,4-tetrahydroisoquinoline) derivatives [J].

Craig, DC ;

Judeh, ZMA ;

Read, RW .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2002, 55 (11) :733-736

[7] Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to (2-pyridyl)sulfonyl imines of chalcones [J].

Esquivias, J ;

Arrayás, RG ;

Carretero, JC .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7451-7454

[8] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition [J].

Feringa, BL .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :346-353

[9] Copper-catalyzed asymmetric conjugate addition of Grignard reagents to cyclic enones [J].

Feringa, BL ;

Badorrey, R ;

Peña, D ;

Harutyunyan, SR ;

Minnaard, AJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) :5834-5838

[10] The first Bischler-Napieralski cyclization in a room temperature ionic liquid [J].

Judeh, ZMA ;

Ching, CB ;

Bu, J ;

McCluskey, A .

TETRAHEDRON LETTERS, 2002, 43 (29) :5089-5091

← 1 2 3 4 →