Synthesis and applications of masked oxo-sulfinamides in asymmetric synthesis

Organic & Biomolecular Chemistry
Ramakrishna Edupuganti, Franklin A Davis

Abstract

This short perspective reports on the synthesis and applications of a class of chiral amino carbonyl compounds, masked oxo-sulfinamides where the amine is protected with an N-sulfinyl moiety and the carbonyl group is protected as the ketal or 1,3-dithiane. These polyfunctionalized chiral building blocks are prepared by addition of organometallic reagents to masked oxo-sulfinimines (N-sulfinyl imines) or the addition of oxo-organometallic reagents and lithio-1,3-dithianes to sulfinimines. Because unmasking of the amino and carbonyl groups results in cyclic imines, these chiral building blocks are particularly useful for the asymmetric synthesis of functionalized nitrogen heterocycles, including prolines, pipecolic acids, pyrrolidines, homotropinones, tropinones, and tropane alkaloids such as cocaine and C-1 cocaine analogues.

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Citations

Sep 29, 2015·The Journal of Organic Chemistry·Eunhye LeeChan-Mo Yu
Sep 3, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·José Luis Viveros-CeballosCarlos Cativiela
Jun 14, 2017·Organic Letters·Firas M Al-Saffar, Richard C D Brown
Oct 2, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jasmin BuschClaudia Bizzarri
Jun 8, 2021·Beilstein Journal of Organic Chemistry·Joseane A MendesCamilla D Buarque
Sep 23, 2014·The Journal of Organic Chemistry·Haibo PengJiang Cheng
Aug 18, 2021·The Journal of Organic Chemistry·Chun-Tai HungCheng-Che Tsai
Jan 30, 2013·The Journal of Organic Chemistry·David M HodgsonAmber L Thompson

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