A Bifunctional B, N‐Based Asymmetric Catalytic Nitrostyrene‐Michael Addition Acting through a 10‐Membered Ring Cyclic Transition State. Issue 12 (16th November 2021)

• Record Type: Journal Article
• Authors: Du, Yihao; Sari, Ozlem; Erdem, Safiye S.; Whiting, Andrew
• Is Part Of: Helvetica chimica acta. Volume 104:Issue 12(2021)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-11-16
• Subjects: amino-boronic acid -- asymmetric synthesis -- B, N-bifunctional catalysis -- homoboroproline -- Michael addition -- nitroalkenes; Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.202100199
• Languages: English
• ISSNs: 0018-019X

Abstract

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. Abstract :