Diastereoselective Addition of Prochiral Nucleophilic Alkenes to a-Chiral N-Sulfonyl Imines

29 September 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The Lewis acid catalyzed addition of prochiral E and Z allyl nucleophiles to chiral -alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C2, C3, and C4 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexenes. The C3 and C4 diastereoselectivity (dr) is influenced by the geometry of the alkene, size of N-sulfonyl substituent, and steric bulk of the substituted -alkoxy ether group. This work demonstrates that three of the four possible diastereomers can be synthesized in high diastereoselectivity and high yields using the current methods. A mechanistic computational analysis to elucidate the high selectivity is also presented.

Supplementary materials

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Title
Diastereoselective Addition of Prochiral Nucleophilic Alkenes to-Chiral N-Sulfonyl Imines
Description
Procedures, characterization, X-ray Coordinates and Computational supporting information
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