NHC–manganese(i) complexes as carbene transfer agents

Imidazolium Carboxylates as Versatile and Selective N-Heterocyclic Carbene Transfer Agents: Synthesis, Mechanism, and Applications

Journal of the American Chemical Society ◽

10.1021/ja0742885 ◽

2007 ◽

Vol 129 (42) ◽

pp. 12834-12846 ◽

Cited By ~ 162

Author(s):

Adelina M. Voutchkova ◽

Marta Feliz ◽

Eric Clot ◽

Odile Eisenstein ◽

Robert H. Crabtree

Keyword(s):

Synthesis Mechanism ◽

Carbene Transfer ◽

Transfer Agents

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Facile Synthesis of Silver(I)−Carbene Complexes. Useful Carbene Transfer Agents

Organometallics ◽

10.1021/om9709704 ◽

1998 ◽

Vol 17 (5) ◽

pp. 972-975 ◽

Cited By ~ 786

Author(s):

Harrison M. J. Wang ◽

Ivan J. B. Lin

Keyword(s):

Facile Synthesis ◽

Carbene Complexes ◽

Carbene Transfer ◽

Transfer Agents

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Carbene Transfer Agents, Carbenes, and Related Topics

Organometallic Reaction Mechanisms of the Nontransition Elements ◽

10.1016/b978-0-12-481150-8.50011-1 ◽

1974 ◽

pp. 253-266

Author(s):

Donald S. Matteson

Keyword(s):

Carbene Transfer ◽

Transfer Agents

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General Cyclopropane Assembly via Enantioselective Redox-Active Carbene Transfer to Aliphatic Olefins

10.26434/chemrxiv.7436795 ◽

2018 ◽

Author(s):

Marc Montesinos-Magraner ◽

Matteo Costantini ◽

Rodrigo Ramirez-Contreras ◽

Michael E. Muratore ◽

Magnus J. Johansson ◽

...

Keyword(s):

Total Synthesis ◽

Asymmetric Synthesis ◽

Chemical Space ◽

Synthetic Approach ◽

Asymmetric Cyclopropanation ◽

Redox Active ◽

Wide Range ◽

Leaving Group ◽

Stereoelectronic Properties ◽

Carbene Transfer

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates and reagents, even when targeting similar compounds. This limits the speed and chemical space available for discovery campaigns. Here we introduce a practical and versatile diazocompound, and we demonstrate its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. We found that the redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect enabled the asymmetric cyclopropanation of a wide range of olefins including unactivated aliphatic alkenes, enabling the 3-step total synthesis of (–)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally-differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons<i>.</i>

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