A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State

Du, Yihao; Sari, Ozlem; Erdem, Safiye S.; Whiting, Andrew

doi:10.1002/hlca.202100199

A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State

Du, Yihao; Sari, Ozlem; Erdem, Safiye S.; Whiting, Andrew

Authors

Yihao Du

Ozlem Sari

Safiye S. Erdem

Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor

Abstract

The B,N-bifunctional catalyst homoboroproline has been applied to a catalytic asymmetric nitroalkene-Michael addition to β-nitrostyrene analogues, showing broad substrate tolerance, high conversions and moderate to good asymmetric induction. The ability of homoboroproline to act as an efficient catalyst based on enamine-formation of the secondary amine, coupled with intramolecular Lewis-acid chelation of the nitro function, in a non-FLP manner, to effect efficient and enantioselective catalysis via a proposed large 10-membered ring transition state is remarkable and reinforced by theoretical calculations.

Citation

Du, Y., Sari, O., Erdem, S. S., & Whiting, A. (2021). A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State. Helvetica Chimica Acta, 104(12), Article e2100199. https://doi.org/10.1002/hlca.202100199

Journal Article Type	Article
Acceptance Date	Oct 22, 2021
Online Publication Date	Nov 16, 2021
Publication Date	Dec 21, 2021
Deposit Date	Jan 25, 2022
Publicly Available Date	Nov 16, 2022
Journal	Helvetica Chimica Acta
Print ISSN	0018-019X
Electronic ISSN	1522-2675
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	104
Issue	12
Article Number	e2100199
DOI	https://doi.org/10.1002/hlca.202100199
Public URL	https://durham-repository.worktribe.com/output/1218934

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Copyright Statement
This is the peer reviewed version of the following article: Du, Yihao, Sari, Ozlem, Erdem, Safiye S. & Whiting, Andrew (2021). A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State. Helvetica Chimica Acta 104(12): e2100199, which has been published in final form at https://doi.org/10.1002/hlca.202100199. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.