Diastereoselective Synthesis of trans-β-Amino Cyclohexyl Ketones and trans-3-Amino-4-acyl-tetrahydropyrans from Intramolecular C-Alkylation of ω-Halo-Substituted β-Sulfinamido Ketones

Silambarasan, K and Kesavulu, G and Reddy, AA and Prasad, KR (2022) Diastereoselective Synthesis of trans-β-Amino Cyclohexyl Ketones and trans-3-Amino-4-acyl-tetrahydropyrans from Intramolecular C-Alkylation of ω-Halo-Substituted β-Sulfinamido Ketones. In: Journal of Organic Chemistry .

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Abstract

Reaction of ω-halo-substituted nonracemic β-sulfinamido ketones with NaH afforded the β-amino cyclohexyl ketones in excellent yields and diastereoselectivity, via an intramolecular C-alkylation, α to the carbonyl group. The reaction was found to be general and can be applied for the synthesis of different cyclohexyl amino ketones and tetrahydropyrans possessing amine and acyl substitutions.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	25 Feb 2023 08:28
Last Modified:	25 Feb 2023 08:28
URI:	https://eprints.iisc.ac.in/id/eprint/80702

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