Enantiocontrolled Synthesis of β-Branched α-Amino Acids by Using CuI-Catalyzed 1,4-Addition of Glycine Imines to β-Substituted gem-Diactivated Olefins

被引：25

作者：

Hernandez-Toribio, Jorge ^{[1
]}

Gomez Arrayas, Ramon ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, Fac Ciencias, E-28049 Madrid, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 23期

关键词：

amino acids; asymmetric catalysis; conjugate addition; copper; glycinate imines; ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION; CHIRAL CALCIUM COMPLEXES; DIRECT MANNICH REACTION; AZOMETHINE YLIDES; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; MICHAEL REACTION; SCHIFF-BASES; DERIVATIVES; ESTERS;

D O I：

10.1002/chem.201100374

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Branching out! The catalytic asymmetric conjugate addition of glycinate Schiff bases to β-substituted gem-diactivated Michael acceptors under proton transfer conditions gives a variety of β-branched α-amino acids (see scheme; Dpm=diphenylmethylene, EWG=electron-withdrawing group) with excellent levels of diastereo- (typically syn/anti >90:10) and enantiocontrol (90-99 % ee). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6334 / 6337

页数：4

共 4 条

[1] 1,4-ADDITION OF (DIPHENYLMETHYLENE)AMINE TO ACCEPTOR SUBSTITUTED OLEFINS - A VERSATILE SYNTHESIS OF PROTECTED BETA-AMINO ACIDS, NITRILES, AND KETONES
WESSJOHANN, L
MCGAFFIN, G
DEMEIJERE, A
SYNTHESIS-STUTTGART, 1989, (05): : 359 - 363
[2] Synthesis of unnatural amino acid derivatives via palladium-catalyzed 1,4-addition of boronic acids
Ray, Devalina
Nyong, Abijah M.
Natarajan, Amarnath
TETRAHEDRON LETTERS, 2010, 51 (19) : 2655 - 2656
[3] The synthesis of α-amino-γ-substituted adipic acids:: stereoelectronic effects during the 1,4-addition of organocuprates to methyl N-tert-butoxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate
Muller, M
Schoenfelder, A
Didier, B
Mann, A
Wermuth, CG
CHEMICAL COMMUNICATIONS, 1999, (08) : 683 - 684
[4] Rhodium-Catalyzed Enantioselective 1,4-Addition of Arylboronic Acids to 2,3-Dihydro-4-pyridones Using 4,8-Substituted Bicyclo[3.3.1]nona-2,6-dienes as Ligands
Stoncius, Sigitas
Sadzeviciene, Rita
Labanauskas, Linas
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (09)

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