Organic Letters
Organic Letters
5 years ago

Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine

Multicomponent cis- and trans-Aziridinatons in the Syntheses of All Four Stereoisomers of Sphinganine
Munmun Mukherjee, Anil K. Gupta, William D. Wulff, Yubai Zhou
All four stereoisomers of sphinganine can be synthesized by a multicomponent aziridination of an aldehyde, an amine and an α-diazo carbonyl compound mediated by a BOROX catalyst with high asymmetric induction (≥96% ee). The threo isomers are available from ring-opening of cis-aziridines by an oxygen nucleophile with inversion at the C-3 position and the erythro-isomers are likewise available from trans-aziridines.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00697

DOI: 10.1021/acs.orglett.7b00697

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