Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

Romanov Michailidis, Fedor; Pupier, Marion; Besnard, Céline; Buergi, Thomas; Alexakis, Alexandre

doi:10.1021/ol5022355

Scientific article

English

Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

Contributors

Romanov Michailidis, Fedor; Pupier, Marion; Besnard, Céline; Buergi, Thomas; Alexakis, Alexandre

Published in

Organic letters, vol. 16, no. 19, p. 4988-4991

Publication date

2014

Abstract

An efficient and highly stereoselective fluorinative aza-semipinacol rearrangement is described. The catalytic reaction requires use of Selectfluor in combination with the chiral, enantiopure phosphate anion derived from acid L3. Under optimized conditions, cyclopropylamines A were transformed into β-fluoro cyclobutylimines B in good yields and high levels of diastereo- and enantiocontrol. Furthermore, the optically active cyclobutylimines were reduced diastereoselectively with L-Selectride in the corresponding fluorinated amines C, compounds of significant interest in the pharmacological industry.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

ROMANOV MICHAILIDIS, Fedor et al. Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement. In: Organic letters, 2014, vol. 16, n° 19, p. 4988–4991. doi: 10.1021/ol5022355

Article (Published version)

Identifiers

PID : unige:41312
DOI : 10.1021/ol5022355

Journal ISSN

1523-7052

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Creation

28/10/2014 15:09:00

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28/10/2014 15:09:00

Update

14/03/2023 22:10:59

Status update

14/03/2023 22:10:59

Last indexation

30/10/2024 20:31:08

Enantioselective Catalytic Fluorinative Aza-semipinacol Rearrangement

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

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Identifiers

Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation