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

創薬科学部門

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

10 被引用数 (Scopus)

抄録

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.

本文言語	英語
ページ（範囲）	8962-8965
ページ数	4
ジャーナル	Organic letters
巻	21
号	22
DOI	https://doi.org/10.1021/acs.orglett.9b03347
出版ステータス	出版済み - 11月 15 2019

!!!All Science Journal Classification (ASJC) codes

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.9b03347

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

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.}",

note = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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day = "15",

doi = "10.1021/acs.orglett.9b03347",

language = "English",

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T1 - Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides

T2 - Access to Fully Substituted α-Amino Ketones

AU - Velasco-Rubio, Álvaro

AU - Alexy, Eric J.

AU - Yoritate, Makoto

AU - Wright, Austin C.

AU - Stoltz, Brian M.

PY - 2019/11/15

Y1 - 2019/11/15

N2 - 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.

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

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!!!All Science Journal Classification (ASJC) codes

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