Catalytic asymmetric C-Si bond formation to acyclic α,β-unsaturated acceptors by RhI-catalyzed conjugate silyl transfer using a Si-B linkage

被引：100

作者：

Walter, Christian ^{[1
]}

Oestreich, Martin ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 20期

关键词：

asymmetric catalysis; boron; homogeneous catalysis; rhodium; silicon;

D O I：

10.1002/anie.200800361

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A perfect match: The RhI-catalyzed conjugate silylation of acyclic Z-configured α,β-unsaturated carboxyl compounds including imides with silylboronic ester yields almost enantiopure α-chiral quaternary silanes (see scheme; R=aryl and (branched) alkyl, cod=cycloocta-1,5-diene, pin=pinacolato). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3818 / 3820

页数：3

共 8 条

[1] Metal-Free Catalytic C-Si Bond Formation in an Aqueous Medium. Enantioselective NHC-Catalyzed Silyl Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls
O'Brien, Jeannette M.
Hoveyda, Amir H.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7712 - 7715
[2] Copper(II)-Catalyzed Silyl Conjugate Addition to α,β-Unsaturated Conjugated Compounds: Bronsted Base-Assisted Activation of Si-B Bond in Water
Calderone, Joseph A.
Santos, Webster L.
ORGANIC LETTERS, 2012, 14 (08) : 2090 - 2093
[3] Catalytic asymmetric C-Si bond activation via torsional strain-promoted Rh-catalyzed aryl-Narasaka acylation
Feng, Jia
Bi, Xiufen
Xue, Xiaoping
Li, Na
Shi, Lei
Gu, Zhenhua
NATURE COMMUNICATIONS, 2020, 11 (01)
[4] Nickel-Catalyzed Decarboxylative C-Si Bond Formation: A Regioselective Cross-Coupling Between Trialkyl Silanes and α,β-Unsaturated Carboxylic Acids
Allam, Bharat Kumar
Azeez, Sadaf
Kandasamy, Jeyakumar
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (11)
[5] Efficient C-B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls
Lee, Kang-sang
Zhugralin, Adil R.
Hoveyda, Amir H.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (21) : 7253 - +
[6] Efficient C-B bond formation promoted by N-heterocyclic carbenes: Synthesis of tertiary and quaternary B-substituted carbons through metal-free catalytic boron conjugate additions to cyclic and acyclic α,β,-unsaturated carbonyls
Lee, Kang-sang
Hoveyda, Amir H.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[7] Efficient C-B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated Carbonyls (vol 131, pg 7253, 2009)
Lee, Kang-sang
Zhugralin, Adil R.
Hoveyda, Amir H.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (36) : 12766 - 12766
[8] Correction to: Intermediacy of Ni-Ni Species in sp2 C-O Bond Cleavage of Aryl Esters: Relevance in Catalytic C-Si Bond Formation (Journal of the American Chemical Society (2018) 140:28 (8771−8780) DOI: 10.1021/jacs.8b04479)
Somerville, Rosie J.
Hale, Lillian V. A.
Gómez-Bengoa, Enrique
Burés, Jordi
Martin, Ruben
Journal of the American Chemical Society, 2019, 141 (51):

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