Selective Michael Reaction Controlled by Supersilyl Protecting Group

Izumiseki, Atsuto; Yamamoto, Hisashi

doi:10.1002/ange.201503574

Angewandte Chemie

2015

DOI: 10.1002/ange.201503574

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Selective Michael Reaction Controlled by Supersilyl Protecting Group

Atsuto Izumiseki

Hisashi Yamamoto

Abstract: Selective Michael reaction of organolithium reagents to supersilyl methacrylate is reported. The method was able to control as ingle and double Michael addition. The successful termination of the process using the supersilyl protecting group allows for the controlled, chemoselective,a nd diastereoselective Michael reaction.

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Cited by 4 publications

References 44 publications

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Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions

Yuan

Zheng

et al. 2018

Adv Synth Catal

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The development of new strategies or reaction processes that tease new reactivity of functional groups continues to spur synthetic chemists toward innovative solutions that access new compounds. Herein, we find that the silicon‐based bulky group enables a 1,3‐dipolar addition−initiated parallel kinetic resolution (PKR) to occur unexpectedly, leading to the highly enantioselective synthesis of two structurally different types of amino acid derivatives via chemodivergent [3+2] cycloaddition reactions and tandem conjugate addition‐elimination reaction respectively. The resulting and structurally divergent enantioenriched amino acid derivatives that contain four contiguous stereogenic centers and an all‐carbon quaternary center were obtained with up to 99% ee with >95:1 dr and good yields.magnified image

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Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions

Yuan

Zheng

et al. 2018

Adv Synth Catal

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Enantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues

Korotkov

Chapman

et al. 2016

Angewandte Chemie

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Concise, scalable, and enantioselective formal syntheses of eight dimeric and three monomeric nuphar alkaloids were achieved, along with the construction of a stereochemically diverse collection of the first known monomeric analogues having apoptotic activity. The syntheses involved the development of highly enantioselective Brønsted acid catalyzed vinylogous Mukaiyama–Mannich reactions, which feature the unprecedented use of a supersilyl group to control the regio‐, enantio‐ and diastereoselectivity. Biological studies reveal that several of these novel nuphar analogues are even more potent than their dimeric natural product counterparts.

show abstract

Enantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues

Korotkov

Chapman

et al. 2016

Angew Chem Int Ed

View full text Add to dashboard Cite

Concise, scalable, and enantioselective formal syntheses of eight dimeric and three monomeric nuphar alkaloids were achieved, along with the construction of a stereochemically diverse collection of the first known monomeric analogues having apoptotic activity. The syntheses involved the development of highly enantioselective Brønsted acid catalyzed vinylogous Mukaiyama-Mannich reactions, which feature the unprecedented use of a supersilyl group to control the regio-, enantio- and diastereoselectivity. Biological studies reveal that several of these novel nuphar analogues are even more potent than their dimeric natural product counterparts.

show abstract

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Selective Michael Reaction Controlled by Supersilyl Protecting Group

Cited by 4 publications

References 44 publications

Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions

Silicon‐based Bulky Group−Tuned Parallel Kinetic Resolution in Copper‐Catalyzed 1,3‐Dipolar Additions

Enantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues

Enantioselective Formal Syntheses of 11 Nuphar Alkaloids and Discovery of Potent Apoptotic Monomeric Analogues

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