Point to Axial Chirality Transfer: Asymmetric Synthesis of Substi-tuted 1-Aza-Spiro [2,3]-Hexanes and Spiro Thiazolidinethiones

02 July 2025, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Synthesis of chiral 1-aza-spiro [2,3]-hexanes and spiro thiazolidinethiones possessing axial as well as point chirality was accomplished by transfer of point group chirality to axial chirality without losing the point chirality. The process involved Cs2CO3 mediated ring opening of the bicyclobutane derivatives containing the chiral sulfinamides prepared from Ellman sulfin-imines. The procedure is operationally simple, does not involve either expensive multi-metal catalysis or arduous experimental procedures/ transformations.

Keywords

axial chirality
sulfinimines
carbanions
bicyclobutanes

Supplementary materials

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Title
Point to Axial Chirality Transfer: Asymmetric Synthesis of Substituted 1-Aza-Spiro [2,3]-Hexanes and Spiro Thiazolidinethiones
Description
Supporting Information. Experimental procedures and copies of the NMR spectra of all new compounds is available in the Supporting Information. This material is available free of charge via the Internet at http://pubs.acs.org
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