Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides: Access to Fully Substituted α-Amino Ketones

Álvaro Velasco-Rubio; Eric J. Alexy; Makoto Yoritate; Austin C. Wright; Brian M. Stoltz

doi:10.1021/acs.orglett.9b03347

Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides: Access to Fully Substituted α-Amino Ketones

Álvaro Velasco-Rubio, Eric J. Alexy, Makoto Yoritate, Austin C. Wright, Brian M. Stoltz

Department of Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

A versatile thermal Overman rearrangement of enantioenriched, cyclic allylic alcohols providing tertiary allylic amines has been developed. The vinyl bromide used to control enantioselectivity in a preceding CBS reduction is utilized as a synthetic handle for the preparation of tertiary α-amino ketones and related derivatives in an asymmetric fashion.

Original language	English
Pages (from-to)	8962-8965
Number of pages	4
Journal	Organic letters
Volume	21
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.9b03347
Publication status	Published - Nov 15 2019

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b03347

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abstract = "A versatile thermal Overman rearrangement of enantioenriched, cyclic allylic alcohols providing tertiary allylic amines has been developed. The vinyl bromide used to control enantioselectivity in a preceding CBS reduction is utilized as a synthetic handle for the preparation of tertiary α-amino ketones and related derivatives in an asymmetric fashion.",

author = "{\'A}lvaro Velasco-Rubio and Alexy, {Eric J.} and Makoto Yoritate and Wright, {Austin C.} and Stoltz, {Brian M.}",

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AU - Alexy, Eric J.

AU - Yoritate, Makoto

AU - Wright, Austin C.

AU - Stoltz, Brian M.

PY - 2019/11/15

Y1 - 2019/11/15

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AB - A versatile thermal Overman rearrangement of enantioenriched, cyclic allylic alcohols providing tertiary allylic amines has been developed. The vinyl bromide used to control enantioselectivity in a preceding CBS reduction is utilized as a synthetic handle for the preparation of tertiary α-amino ketones and related derivatives in an asymmetric fashion.

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Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides: Access to Fully Substituted α-Amino Ketones

Abstract

All Science Journal Classification (ASJC) codes

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