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Highly enantioselective organocatalytic cyclopropanation of enals using benzyl chlorides

Highly enantioselective organocatalytic cyclopropanation of enals using benzyl chlorides
Highly enantioselective organocatalytic cyclopropanation of enals using benzyl chlorides
Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.
0022-3263
3488-3500
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Ashe, Maria
ff483cdd-7878-4ae2-96e5-c21a42581651
Shin, Hun
9d433708-6658-45da-9c9b-3de3a87acbf5
Yang, Hye
dc5d2290-8d73-4973-a591-ed58df23c22d
Mazzanti, Andrea
1e31a7a1-e163-4bd4-9e72-42bc64f60277
Yang, Jung Woon
70327194-b21c-402c-83c0-4474fb47db63
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Ashe, Maria
ff483cdd-7878-4ae2-96e5-c21a42581651
Shin, Hun
9d433708-6658-45da-9c9b-3de3a87acbf5
Yang, Hye
dc5d2290-8d73-4973-a591-ed58df23c22d
Mazzanti, Andrea
1e31a7a1-e163-4bd4-9e72-42bc64f60277
Yang, Jung Woon
70327194-b21c-402c-83c0-4474fb47db63
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

Meazza, Marta, Ashe, Maria, Shin, Hun, Yang, Hye, Mazzanti, Andrea, Yang, Jung Woon and Rios Torres, Ramon (2016) Highly enantioselective organocatalytic cyclopropanation of enals using benzyl chlorides. Journal of Organic Chemistry, 81 (9), 3488-3500. (doi:10.1021/acs.joc.5b02801).

Record type: Article

Abstract

Herein, we describe the first enantioselective cyclopropanation of enals using benzyl chlorides as bifunctional (nucleophilic and electrophilic) reagents. The reaction is simply catalyzed by chiral secondary amines to afford the formyl cyclopropane derivatives in good yields with moderate to excellent stereoselectivities.

Text
Manuscript (Jung Woon Yang & Ramon Rios).pdf - Accepted Manuscript
Available under License University of Southampton Accepted Manuscript Licence.
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More information

Accepted/In Press date: 14 April 2016
e-pub ahead of print date: 15 April 2016
Published date: 6 May 2016
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow
Learn more about School of Chemistry research

Identifiers

Local EPrints ID: 396478
URI: http://eprints.soton.ac.uk/id/eprint/396478
DOI: doi:10.1021/acs.joc.5b02801
ISSN: 0022-3263
PURE UUID: cb0defa6-acec-43fd-8ab0-92dcb867352c
ORCID for Marta Meazza: ORCID iD orcid.org/0000-0003-4382-0626
ORCID for Ramon Rios Torres: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 09 Jun 2016 14:10
Last modified: 15 Mar 2024 05:38

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Contributors

Author: Marta Meazza ORCID iD
Author: Maria Ashe
Author: Hun Shin
Author: Hye Yang
Author: Andrea Mazzanti
Author: Jung Woon Yang
Author: Ramon Rios Torres ORCID iD

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