Highly Enantioselective Intramolecular Copper Catalyzed C-H Insertion Reactions of α-Diazosulfones

被引：61

作者：

Flynn, Christopher J. ^{[1
]}

Elcoate, Curtis J. ^{[1
]}

Lawrence, Simon E. ^{[1
]}

Maguire, Anita R. ^{[1
,2
]}

机构：

[1] Natl Univ Ireland Univ Coll Cork, Dept Chem, Cork, Ireland

[2] Natl Univ Ireland Univ Coll Cork, Sch Pharm, Analyt & Biol Chem Res Facil, Cork, Ireland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 04期

关键词：

RHODIUM CARBENOID INSERTIONS; CARBON-HYDROGEN INSERTION; BETA-KETO SULFONES; CYCLOPROPANATION; BONDS; HETEROCYCLES;

D O I：

10.1021/ja909713a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Excellent enantiocontrol (up to 98% ee) is achieved in copper catalyzed C-H insertions of alpha-diazosulfones to form thiopyrans, with up to 60% ee in C-H insertions leading to sulfolanes.

引用

页码：1184 / +

页数：4

共 50 条

[21] Palladium(II)-Catalyzed Highly Enantioselective C-H Arylation of Cyclopropylmethylamines
Chan, Kelvin S. L.
Fu, Hai-Yan
Yu, Jin-Quan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (05) : 2042 - 2046
[22] Enantioselective intramolecular C-H insertion route to a key intermediate for the synthesis of trinem antibiotics
Anada, M
Hashimoto, S
TETRAHEDRON LETTERS, 1998, 39 (49) : 9063 - 9066
[23] Enantioselective Intramolecular C-H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach
Zhu, Dong
Ma, Jun
Luo, Kui
Fu, Hongguang
Zhang, Li
Zhu, Shifa
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (29) : 8452 - 8456
[24] CONSTRUCTION OF BETA-LACTAMS BY HIGHLY SELECTIVE INTRAMOLECULAR C-H INSERTION FROM RHODIUM(II) CARBOXYLATE CATALYZED-REACTIONS OF DIAZOACETAMIDES
DOYLE, MP
SHANKLIN, MS
OON, SM
PHO, HQ
VANDERHEIDE, FR
VEAL, WR
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14): : 3384 - 3386
[25] Simple and efficient heterogeneous copper catalysts for enantioselective C-H carbene insertion
Fraile, Jose M.
Garcia, Jose I.
Mayoral, Jose A.
Roldan, Marta
ORGANIC LETTERS, 2007, 9 (04) : 731 - 733
[26] Stereochemical Outcome of Copper-Catalyzed C-H Insertion Reactions. An Experimental and Theoretical Study
Jimenez-Oses, Gonzalo
Vispe, Eugenio
Roldan, Marta
Rodriguez-Rodriguez, Sergio
Lopez-Ram-de-Viu, Pilar
Salvatella, Luis
Mayoral, Jose A.
Fraile, Jose M.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (12): : 5851 - 5857
[27] Copper-Catalyzed Highly Enantioselective Carbenoid Insertion into Si-H Bonds
Zhang, Yong-Zhen
Zhu, Shou-Fei
Wang, Li-Xin
Zhou, Qi-Lin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) : 8496 - 8498
[28] Copper Catalyzed C-H Functionalization for Direct Mannich Reactions
Rueping, Magnus
Tolstoluzhsky, Nikita
ORGANIC LETTERS, 2011, 13 (05) : 1095 - 1097
[29] Enantioselective intramolecular C-H insertion reaction catalyzed by dirhodium(II) carboxylates: Catalytic, asymmetric construction of 2-azetidinones
Anada, M
Watanabe, N
Washimoto, S
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 224 - ORGN
[30] Palladium(0)-Catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C-H Bonds
Melot, Romain
Zuccarello, Marco
Cavalli, Diana
Niggli, Nadja
Devereux, Michael
Burgi, Thomas
Baudoin, Olivier
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 7245 - 7250

← 1 2 3 4 5 →