Catalytic Carbon Insertion into the β-Vinyl C-H Bond of Cyclic Enones with Alkyl Diazoacetates

被引：29

作者：

Lee, Sung Il ^{[1
,2
]}

Kang, Byung Chul ^{[1
]}

Hwang, Geum-Sook ^{[2
]}

Ryu, Do Hyun ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

[2] Korea Basic Sci Inst, Seoul 136713, South Korea

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 07期

关键词：

ALPHA-SUBSTITUTED ACROLEINS; ASYMMETRIC ROSKAMP REACTION; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; DIAZOESTERS; KETONES; CONSTRUCTION; CYCLOPROPANATION; CONVERSION; PRECURSOR;

D O I：

10.1021/ol4000026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of the boron Lewis acid catalyzed C-SP2-H functionalization of cyclic enones was achieved using diazoacetates. The insertion of the carbon atom of diazoacetates utilizes BF3 center dot Et2O or a newly designed oxazaborolidinium ion as a catalyst to afford beta-functionalized cyclic enones from simple cyclic enones In a single step and high yields. The reaction mechanism was investigated with deuterium labeled 2-cyclohexen-1-one.

引用

页码：1428 / 1431

页数：4

共 50 条

[1] Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones
Lee, Sung Il
Hwang, Geum-Sook
Ryu, Do Hyun
Journal of the American Chemical Society, 2013, 135 (19): : 7126 - 7129
[2] Catalytic Enantioselective Carbon Insertion into the β-Vinyl C-H Bond of Cyclic Enones
Lee, Sung Il
Hwang, Geum-Sook
Ryu, Do Hyun
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) : 7126 - 7129
[3] Catalytic asymmetric C-H insertion reactions of vinyl carbocations
Nistanaki, Sepand K.
Williams, Chloe G.
Wigman, Benjamin
Wong, Jonathan J.
Haas, Brittany C.
Popov, Stasik
Werth, Jacob
Sigman, Matthew S.
Houk, K. N.
Nelson, Hosea M.
SCIENCE, 2022, 378 (6624) : 1085 - 1091
[4] Formal Nitrene Insertion into the β-Vinyl C-H Bond of Acroleins: Synthesis of Enaminals
Zhang, Dongsheng
Zheng, Huatao
Zeng, Lei
Nie, Yi
Fan, Yingzhu
Rao, Weidong
Gao, Lizhu
ORGANIC LETTERS, 2023, 25 (01) : 179 - 183
[5] Insertion of methylidyne into the C-H bond of ethylene
Wang, ZX
Huang, MB
CHEMICAL PHYSICS LETTERS, 1998, 291 (3-4) : 381 - 386
[6] Catalytic Carbene Insertion into C-H Bonds
Doyle, Michael P.
Duffy, Richard
Ratnikov, Maxim
Zhou, Lei
CHEMICAL REVIEWS, 2010, 110 (02) : 704 - 724
[7] REACTIONS OF ATOMIC CARBON WITH SIMPLE HYDROCARBONS - EVIDENCE FOR C-H BOND INSERTION
MACKAY, C
WOLFGANG, R
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (10) : 2399 - &
[8] Studies in catalytic C-H amination involving nitrene C-H insertion
Collet, Florence
Lescot, Camille
Liang, Chungen
Dauban, Philippe
DALTON TRANSACTIONS, 2010, 39 (43) : 10401 - 10413
[9] Diverse Alkanones by Catalytic Carbon Insertion into the Formyl C-H Bond. Concise Access to the Natural Precursor of Achyrofuran
Wommack, Andrew J.
Moebius, David C.
Travis, Austin L.
Kingsbury, Jason S.
ORGANIC LETTERS, 2009, 11 (15) : 3202 - 3205
[10] Stereocontrolled polyol synthesis via C-H insertion reactions of silicon tethered diazoacetates
Kablean, SN
Marsden, SP
Craig, AM
TETRAHEDRON LETTERS, 1998, 39 (28) : 5109 - 5112

← 1 2 3 4 5 →