Issue 12, 2024

Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds

Abstract

Aza-[4 + 2] annulation reactions between α-vinyl Morita–Baylis–Hillman (MBH) adducts and cyclic imines have been developed, achieving regiodivergent synthesis of two distinct types of azatricyclic products. The process initiates with an SN2′′ addition of triphenylphosphine to the MBH adducts, forming a pentadienyl phosphonium intermediate. This intermediate then undergoes aza-[4 + 2] annulation with saccharin-derived ketimines to yield sultam-fused tetrahydropyridines with exomethylene groups in moderate to good yields. Alternatively, employing DABCO and trifluoroacetic acid facilitates an aza-[4 + 2] annulation with 3,4-dihydroisoquinoline, resulting in the formation of exomethylene-bearing benzoquinolizidines with reversed orientational regioselectivity.

Graphical abstract: Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds

Supplementary files

Article information

Article type
Research Article
Submitted
06 Feb 2024
Accepted
27 Apr 2024
First published
29 Apr 2024

Org. Chem. Front., 2024,11, 3415-3420

Aza-[4 + 2] annulations of α-vinyl Morita–Baylis–Hillman adducts for regiodivergent synthesis of exomethylene-bearing azatricyclic compounds

Y. Liu, C. Li, C. Huang, L. Zhu, G. Xiong, Y. Zhu, S. Fan, J. Dai and H. Xiao, Org. Chem. Front., 2024, 11, 3415 DOI: 10.1039/D4QO00255E

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