Organocatalytic asymmetric assembly reactions for the syntheses of carbohydrate derivatives by intermolecular Michael-Henry reactions.

Proceedings of the National Academy of Sciences of the United States of America
Hisatoshi UeharaCarlos F Barbas

Abstract

Given the significance of carbohydrates in life, medicine, and industry, the development of simple and efficient de novo methods to synthesize carbohydrates are highly desirable. Organocatalytic asymmetric assembly reactions are powerful tools to rapidly construct molecules with stereochemical complexity from simple precursors. Here, we present a simple and robust methodology for the asymmetric synthesis of pyranose derivatives with talo- and manno- configurations from simple achiral precursors through organocatalytic asymmetric intermolecular Michael-Henry reaction sequences. In this process, (tert-butyldimethylsilyloxy)acetaldehyde 1 was successfully utilized in two ways: as a donor in a highly selective anti-Michael reaction and as an acceptor in a consecutive Henry reaction. Varied nitroolefins served as Michael acceptors and varied aldehydes substituted for 1 as Henry acceptors providing for the construction of a wide range of carbohydrates with up to 5 stereocenters. In these reactions, a catalyst-controlled Michael reaction followed by a substrate-controlled Henry reaction provided 3,4-dideoxytalose derivatives 6 in a highly stereoselective manner. The Henry reaction was affected by addition of a simple base such as trie...Continue Reading

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Citations

Apr 12, 2011·Organic Letters·Shaik AnwarKwunmin Chen
Oct 1, 2011·Chemical Communications : Chem Comm·Fang WangYun-Bao Jiang
Dec 2, 2010·Proceedings of the National Academy of Sciences of the United States of America·Eric N Jacobsen, David W C MacMillan
Feb 1, 2016·Chemical Science·Yujiro Hayashi
Dec 17, 2015·Chemistry : a European Journal·Sun Min KimJung Woon Yang
Jul 19, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xiang LiBo Han
Sep 17, 2013·Angewandte Chemie·Tyler J AuvilAnita E Mattson
Oct 12, 2013·Chemistry : a European Journal·Ulf Scheffler, Rainer Mahrwald
Jul 10, 2020·Organic & Biomolecular Chemistry·Tasneem ParvinLokman H Choudhury
Jan 19, 2012·Angewandte Chemie·Bhoopendra TiwariYonggui Robin Chi
Apr 21, 2012·Chemical Communications : Chem Comm·José G Hernández, Eusebio Juaristi
Jun 26, 2014·Organic & Biomolecular Chemistry·Guobing YanLianggui Wang
Oct 5, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Wan-Yun HuangKwunmin Chen
Feb 9, 2013·Chemical Communications : Chem Comm·Michail TsakosChristoforos G Kokotos

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