Asymmetric -Amination Reaction of Alkenoate Cyclic Esters Catalyzed by Chiral Tin Alkoxides

被引：3

作者：

Yanagisawa, Akira ^{[1
]}

Yamashita, Yoshiki ^{[1
]}

Uchiyama, Chika ^{[1
]}

Nakano, Ryuta ^{[1
]}

Horiguchi, Moe ^{[1
]}

Ida, Kazuki ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Sci, Dept Chem, Mol Chiral Res Ctr,Soft Mol Activat Res Ctr,Inage, Chiba 2638522, Japan

来源：

SYNLETT | 2019年 / 30卷 / 06期

关键词：

alkenoate cyclic esters; lactones; amination; asymmetric catalysis; dialkyl azodicarboxylates; tin catalysis; ELECTROPHILIC ALPHA-AMINATION; BETA-KETO-ESTERS; ENANTIOSELECTIVE AMINATION; ALDEHYDES; CYANOACETATES; COMPLEXES; FUNCTIONALIZATION; DEAROMATIZATION; 2-NAPHTHOLS; COPPER(II);

D O I：

10.1055/s-0037-1612278

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic enantioselective -amination reaction of alkenoate cyclic esters with dialkyl azodicarboxylates was achieved by using a 3,3-di(1-naphthyl)-substituted ( R )-BINOL-dibromostannane complex as a chiral precatalyst in the presence of a sodium alkoxide and an alcohol. Optically active -hydrazino ketones were obtained in moderate to high yields and with up to 91% ee in the presence of the chiral tin alkoxide generated in situ.

引用

页码：738 / 742

页数：5

共 50 条

[41] ASYMMETRIC INTRAMOLECULAR ENE REACTION CATALYZED BY A CHIRAL TITANIUM ALKOXIDE
NARASAKA, K
HAYASHI, Y
SHIMADA, S
CHEMISTRY LETTERS, 1988, (10) : 1609 - 1612
[42] Asymmetric Henry Reaction Catalyzed by a Chiral Dinuclear Nickel Complex
Liu, Yajun
Deng, Ping
Li, Xiangyang
Xiong, Yan
Zhou, Hui
SYNLETT, 2014, 25 (12) : 1735 - 1738
[43] ASYMMETRIC OXIDATION OF BETA-KETO-ESTERS USING CHIRAL CYCLIC DIOLS
KATO, K
SUEMUNE, H
SAKAI, K
TETRAHEDRON LETTERS, 1994, 35 (19) : 3103 - 3104
[44] Chiral palladium(II)-catalyzed asymmetric glyoxylate-ene reaction:: Alternative approach to the enantioselective synthesis of α-hydroxy esters
Hao, J
Hatano, M
Mikami, K
ORGANIC LETTERS, 2000, 2 (25) : 4059 - 4062
[45] Synthesis of Chiral Esters via Asymmetric Wolff Rearrangement. Reaction
Meng, Jing
Ding, Wei-Wei
Han, Zhi-Yong
ORGANIC LETTERS, 2019, 21 (24) : 9801 - 9805
[46] Practical copper-catalyzed asymmetric synthesis of chiral chrysanthemic acid esters
Itagaki, Makoto
Suenobu, Katsuhiro
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (03) : 509 - 518
[47] ASYMMETRIC ADDITION OF ARYLLITHIUMS TO NAPHTHALENE BHA-ESTERS CATALYZED BY A CHIRAL LIGAND
TOMIOKA, K
SHINDO, M
KOGA, K
TETRAHEDRON LETTERS, 1993, 34 (04) : 681 - 682
[48] Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates
Suzuki, S
Furuno, H
Yokoyama, Y
Inanaga, J
TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 504 - 507
[49] Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL.: Synthesis of α-methyl amino acids
Belokon, YN
Kochetkov, KA
Churkina, TD
Ikonnikov, NS
Chesnokov, AA
Larionov, OV
Kagan, HV
RUSSIAN CHEMICAL BULLETIN, 1999, 48 (05) : 917 - 923
[50] Enantioselective Synthesis of β-Arylamines via Chiral Phosphoric Acid-Catalyzed Asymmetric Reductive Amination
Kim, Kyung-Hee
Lee, Chun-Young
Cheon, Cheol-Hong
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (12): : 6367 - 6374

← 1 2 3 4 5 →