Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium-Catalyzed Conjugate Hydrosilylation

被引：50

作者：

Naganawa, Yuki ^{[1
]}

Kawagishi, Mayu ^{[1
]}

Ito, Jun-ichi ^{[1
]}

Nishiyama, Hisao ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 24期

基金：

日本学术振兴会;

关键词：

asymmetric synthesis; desymmetrization; hydrosilylation; quaternary centers; rhodium; ENANTIOSELECTIVE CONSTRUCTION; NATURAL-PRODUCTS; FACILE SYNTHESIS; HECK ARYLATIONS; REDUCTION; DESYMMETRIZATION; ESTERS; TRANSFORMATIONS; STEREOCENTERS; BEARING;

D O I：

10.1002/anie.201601636

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective desymmetrizing conjugate hydrosilylation of prochiral differently gamma, gamma-disubstituted cyclohexadienone derivatives 2 to furnish the corresponding cyclohexenones 4 with a remote chiral all-carbon quaternary center at the g position is described. Chiral rhodium-bis(oxazolinyl)-phenyl complexes 1 were effective catalysts for this transformation. This catalytic system was extended to the asymmetric transformation of spirocarbocyclic cyclohexadienones 5 to give the corresponding products 6 with high enantiomeric ratios.

引用

页码：6873 / 6876

页数：4

共 50 条

[21] Synthesis of dialkoxydiphenylsilanes via the rhodium-catalyzed hydrosilylation of aldehydes
Nogues, Christophe
Argouarch, Gilles
TETRAHEDRON LETTERS, 2019, 60 (40)
[22] Effect of triarylphosphane ligands on the rhodium-catalyzed hydrosilylation of alkene
Xue, Mei
Li, Jiayun
Peng, Jiajian
Bai, Ying
Zhang, Guodong
Xiao, Wenjun
Lai, Guoqiao
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (02) : 120 - 126
[23] The effect of an acylphosphine ligand on the rhodium-catalyzed hydrosilylation of alkenes
Li, Jiayun
Yang, Chuang
Bai, Ying
Yang, Xiaoling
Liu, Yu
Peng, Jiajian
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 855 : 7 - 11
[24] Rhodium-catalyzed anti-Markovnikov hydrosilylation of alkenes
Liu, Wei
Lu, Wenkui
Yang, Liqun
Wu, Xiaoyu
Zhang, Zhaoguo
TETRAHEDRON, 2022, 109
[25] Effect of silylated triarylphosphine ligands on rhodium-catalyzed hydrosilylation
Li, Jiayun
Xue, Mei
Bai, Ying
Peng, Jiajian
Xiao, Wenjun
APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (11) : 905 - 910
[26] Regiodivergence in rhodium-catalyzed asymmetric hydroboration
Bochat, Andrew
Shoba, Veronika
Chakrabarty, Suman
Hoang, Gia
Wickrama, Rukshani
Palencia, Hector
Takacs, James
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[27] Rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: Synthetic equivalent to asymmetric conjugate alkynylation of enones
Nishimura, Takahiro
Katoh, Taisuke
Takatsu, Keishi
Shintani, Ryo
Hayashi, Tamio
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) : 14158 - +
[28] Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands
Boiteau, JG
Imbos, F
Minnaard, AJ
Feringa, BL
ORGANIC LETTERS, 2003, 5 (05) : 681 - 684
[29] Synthesis of fused oligosiloles by rhodium-catalyzed stitching reaction and subsequent remote conjugate dehydration
Morita, Masaki
Shintani, Ryo
CHEMISTRY LETTERS, 2024, 53 (04)
[30] IMPROVED SYNTHESIS OF DIMETHYLKETENE TRIMETHYLSILYL ACETALS BY RHODIUM-CATALYZED HYDROSILYLATION
REVIS, A
HILTY, TK
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09): : 2972 - 2973

← 1 2 3 4 5 →