Enantioselective 1,4-addition of unmodified ketone catalyzed by a bimetallic Zn-Zn-linked-BINOL complex

被引：67

作者：

Kumagai, N ^{[1
]}

Matsunaga, S ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 26期

关键词：

D O I：

10.1021/ol016981h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 1,4-Addition (Michael addition) of 2-hydroxy-2'-methoxyacetophenone (2) to various alpha,beta -unsaturated ketones was efficiently promoted by a bimetallic Zn-Zn-linked-BINOL complex 3 with good yield (up to 90%) and excellent enantiomeric excess (up to 99% ee). The resulting 2-hydroxy-1,5-diketones were successfully converted to synthetically more versatile esters and amides.

引用

页码：4251 / 4254

页数：4

共 54 条

[1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes [J].

Anand, NK ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9687-9688

[2]

[Anonymous], COMPREHENSIVE ASYMME

[3] STEREOSELECTIVE TOTAL SYNTHESES OF (+/-)-DI-O-METHYL ETHERS OF AGATHARESINOL, SESQUIRIN-A, AND HINOKIRESINOL, AND OF (+/-)-TRI-O-METHYLSEQUIRIN-E, CHARACTERISTIC NORLIGNANS OF CONIFERAE [J].

BERACIERTA, AP ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1257-1263

[4] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[5] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Barbas, CF .

TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444

[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[7] Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes [J].

Evans, DA ;

Scheidt, KA ;

Johnston, JN ;

Willis, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4480-4491

[8] Enantioselective Lewis acid catalyzed Michael reactions of alkylidene malonates.: Catalysis by C2-symmetric bis(oxazoline) copper(II) complexes in the synthesis of chiral, differentiated glutarate esters [J].

Evans, DA ;

Rovis, T ;

Kozlowski, MC ;

Downey, CW ;

Tedrow, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9134-9142

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

Feringa, BL .

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

[10]

Hauser FM, 2001, SYNTHETIC COMMUN, V31, P77

← 1 2 3 4 5 6 →