Enantioselective One-Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction

被引：18

作者：

Sebesta, Radovan ^{[1
]}

Bilcik, Filip ^{[1
]}

Fodran, Peter ^{[1
]}

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, Bratislava 84215, Slovakia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 29期

关键词：

Asymmetric catalysis; Michael addition; Mannich reaction; Copper; Ferrocene; TANDEM; KETONES;

D O I：

10.1002/ejoc.201000773

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric addition of Grignard reagents to cyclohexenone, catalyzed by ferrocene diphosphanes, afforded chiral magnesium enolates. These enolates reacted in a one-pot arrangement with N-benzylidenetoluenesulfonamide to give beta-amino carbonyl compounds with three contiguous stereocenters. Two major diastereoisomers (dr = 60:40) of product with enantioselectivities up to 95 % ee were separated by flash chromatography.

引用

页码：5666 / 5671

页数：6

共 50 条

[21] Catalytic asymmetric conjugate addition of Grignard reagents
Feringa, BL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3172 - U3172
[22] CONJUGATE ADDITION OF GRIGNARD REAGENTS TO SORBOMESITYLENE AND SORBODURENE
FUSON, RC
LIBBY, WH
JOURNAL OF ORGANIC CHEMISTRY, 1951, 16 (04): : 626 - 630
[23] Sequential One-Pot Addition of Excess Aryl-Grignard Reagents and Electrophiles to O-Alkyl Thioformates
Murai, Toshiaki
Morikawa, Kenta
Maruyama, Toshifumi
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (39) : 13112 - 13119
[24] Stereoselective domino conjugate addition of Grignard reagents to lactones followed by reaction with activated alkenes catalyzed by ferrocenyl carbene ligands
Soradova, Zuzana
Mazikova, Jana
Meciarova, Maria
Sebesta, Radovan
TETRAHEDRON-ASYMMETRY, 2015, 26 (5-6) : 271 - 275
[25] ONE-POT, ONE-CARBON AND MULTICARBON HOMOLOGATION OF ALKYL-HALIDES - REACTION OF GRIGNARD-REAGENTS WITH CHLOROIODOMETHANE
HAHN, RC
TOMPKINS, J
TETRAHEDRON LETTERS, 1990, 31 (07) : 937 - 940
[26] A new one-pot synthesis of macroheterocycles using Mannich reaction
Yang, MM
Zhang, JQ
Shen, Z
CHINESE CHEMICAL LETTERS, 1997, 8 (10) : 845 - 846
[27] A New One-Pot Synthesis of Macroheterocycles Using Mannich Reaction
Min Min YANG
Jin Qi ZHANG
Zhen SHEN (Department of Chemistry
ChineseChemicalLetters, 1997, (10) : 845 - 846
[28] One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides
Suleymanov, Abdusalom A.
Scopelliti, Rosario
Tirani, Farzaneh Fadaei
Severin, Kay
ORGANIC LETTERS, 2018, 20 (11) : 3323 - 3326
[29] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL ZINC(II) COMPLEXES
JANSEN, JFGA
FERINGA, BL
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13): : 4168 - 4175
[30] ONE-POT OXAPROPELLANE SKELETON FORMATION BASED ON CONJUGATE ADDITION
FANG, CL
SUGANUMA, K
SUEMUNE, H
SAKAI, K
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06): : 1549 - 1554

← 1 2 3 4 5 →