Cobalt-Catalyzed Enantioselective and Chemodivergent Addition of Cyclopropanols to Oxabicyclic Alkenes

ACS Catalysis ◽  
2019 ◽  
Vol 9 (6) ◽  
pp. 5638-5644 ◽  
Author(s):  
Junfeng Yang ◽  
Yoshiya Sekiguchi ◽  
Naohiko Yoshikai
Keyword(s):  
Oxabicyclic Alkenes

Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents

2014 ◽  
Vol 12 (13) ◽  
pp. 2080 ◽  
Author(s):  
Dingqiao Yang ◽  
Ni Liang
Keyword(s):  
Ring Opening ◽  
Grignard Reagents ◽  
Oxabicyclic Alkenes

scholarly journals Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives

2013 ◽  
Vol 9 ◽  
pp. 1969-1976 ◽  
Author(s):  
Yin-wei Sun ◽  
Qin Xu ◽  
Min Shi
Keyword(s):  
Gold Catalyst ◽  
Addition Product ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Ethynyl Ketone ◽  
Oxabicyclic Alkenes

Oxabicyclic alkenes can react with electron-deficient terminal alkynes in the presence of a gold catalyst under mild conditions, affording the corresponding addition products in moderate yields. When using alkynyl esters as substrates, the (Z)-acrylate derivatives are obtained. Using but-3-yn-2-one (ethynyl ketone) as a substrate, the corresponding addition product is obtained with (E)-configuration. The proposed mechanism of these reactions is also discussed.

scholarly journals Mechanism, reactivity, and regioselectivity in rhodium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes: a DFT Investigation

2017 ◽  
Vol 7 (1) ◽  
Author(s):  
Zheng-Hang Qi ◽  
Yi Zhang ◽  
Yun Gao ◽  
Ye Zhang ◽  
Xing-Wang Wang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reactions ◽  
Oxabicyclic Alkenes ◽  
Asymmetric Ring Opening

ChemInform Abstract: Copper Phosphoramidite Catalyzed Enantioselective Ring-Opening of Oxabicyclic Alkenes: Remarkable Reversal of Stereocontrol.

ChemInform ◽  
2010 ◽  
Vol 33 (50) ◽  
pp. no-no
Author(s):  
Fabio Bertozzi ◽  
Mauro Pineschi ◽  
Franco Macchia ◽  
Leggy A. Arnold ◽  
Adriaan J. Minnaard ◽  
...  
Keyword(s):  
Ring Opening ◽  
Oxabicyclic Alkenes

Transition Metal-Catalyzed Enantioselective Ring-Opening Reactions of Oxabicyclic Alkenes

2003 ◽  
Vol 36 (1) ◽  
pp. 48-58 ◽  
Author(s):  
Mark Lautens ◽  
Keith Fagnou ◽  
Sheldon Hiebert
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Ring Opening Reactions ◽  
Oxabicyclic Alkenes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Chiral P-Containing Palladacycle-Catalyzed Asymmetric Ring-Opening Reactions of Oxabicyclic Alkenes with Alkenyl Boronic Acids

Synlett ◽  
2011 ◽  
Vol 2011 (07) ◽  
pp. 943-946 ◽  
Author(s):  
Xue-Long Hou ◽  
Xiao-Jun Huang ◽  
Dong-Liang Mo ◽  
Chang-Hua Ding
Keyword(s):  
Ring Opening ◽  
Boronic Acids ◽  
Ring Opening Reactions ◽  
Oxabicyclic Alkenes ◽  
Asymmetric Ring Opening

Palladacycle as Highly Efficient Catalyst for Ring Opening of Oxabicyclic Alkenes with Organozinc Halides.

ChemInform ◽  
2007 ◽  
Vol 38 (35) ◽  
Author(s):  
Ting-Ke Zhang ◽  
Ke Yuan ◽  
Xue-Long Hou
Keyword(s):  
Ring Opening ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Oxabicyclic Alkenes

Rhodium-Catalyzed Allylation Reactions

Synthesis ◽  
2019 ◽  
Vol 51 (13) ◽  
pp. 2585-2631 ◽  
Author(s):  
Mahesh Bhagwan Thoke ◽  
Qiang Kang
Keyword(s):  
Natural Product ◽  
Memory Effect ◽  
Bond Formation ◽  
Allylic Substitution ◽  
Design And Development ◽  
Diverse Range ◽  
Current State ◽  
Drug Synthesis ◽  
Oxabicyclic Alkenes ◽  
Made In

Rhodium-catalyzed allylation reactions are well known for their unique selectivity and reactivity due to the high memory effect of Rh as compared to other metals. These reactions involve the substitution of allylic rhodium intermediates with a diverse range of different nucleophiles, leading to C–C and C–heteroatom bond formation. Modern organic chemists are, however, interested in atom-economical protocols under greener pathways and following recent increased understanding of mechanistic aspects of Rh-catalyzed allylation via the hydrofunctionalization of allenes or alkynes, great strides have made in the design and development of new atom-economical protocols. In this article, we review this field from its beginning to current state.1 Introduction2 Rhodium-Catalyzed Allylic Substitution3 Rhodium-Catalyzed Allylation with Allenes4 Rhodium-Catalyzed Allylation with Alkynes5 Rhodium-Catalyzed Allylation with Dienes6 Rhodium-Catalyzed Allylation by ARO of Oxabicyclic Alkenes7 Rhodium-Catalyzed Enantioselective Allylation in Natural Product and Drug Synthesis8 Conclusion

scholarly journals Palladium-Catalyzed Enantioselective Ring Opening of Oxabicyclic Alkenes with Organozinc Halides.

ChemInform ◽  
2004 ◽  
Vol 35 (46) ◽  
Author(s):  
Ming Li ◽  
Xiao-Xia Yan ◽  
Wei Hong ◽  
Xia-Zhen Zhu ◽  
Bo-Xun Cao ◽  
...  
Keyword(s):  
Ring Opening ◽  
Palladium Catalyzed ◽  
Oxabicyclic Alkenes

Cu(OTf)2-Catalyzed Isomerization of 7-Oxabicyclic Alkenes: A Practical Route to the Synthesis of 1-Naphthol Derivatives

Synthesis ◽  
2008 ◽  
Vol 2008 (19) ◽  
pp. 3043-3046 ◽  
Author(s):  
Zhihui Shao ◽  
Fangzhi Peng ◽  
Baomin Fan ◽  
Xuewei Pu ◽  
Penghui Li ◽  
...  
Keyword(s):  
Oxabicyclic Alkenes ◽  
Naphthol Derivatives
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