Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

A highly regioselective S(N)2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine is developed, which provides an easy access to α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction represents...

Descripción completa

Detalles Bibliográficos
Autores principales: Xu, Silong, Shang, Jian, Zhang, Junjie, Tang, Yuhai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077529/
https://www.ncbi.nlm.nih.gov/pubmed/24991249
http://dx.doi.org/10.3762/bjoc.10.98
_version_ 1782323609003360256
author Xu, Silong
Shang, Jian
Zhang, Junjie
Tang, Yuhai
author_facet Xu, Silong
Shang, Jian
Zhang, Junjie
Tang, Yuhai
author_sort Xu, Silong
collection PubMed
description A highly regioselective S(N)2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine is developed, which provides an easy access to α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction represents the first direct transformation of MBH alcohols into hydrazines.
format Online
Article
Text
id pubmed-4077529
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-40775292014-07-02 Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives Xu, Silong Shang, Jian Zhang, Junjie Tang, Yuhai Beilstein J Org Chem Letter A highly regioselective S(N)2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine is developed, which provides an easy access to α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction represents the first direct transformation of MBH alcohols into hydrazines. Beilstein-Institut 2014-04-30 /pmc/articles/PMC4077529/ /pubmed/24991249 http://dx.doi.org/10.3762/bjoc.10.98 Text en Copyright © 2014, Xu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Xu, Silong
Shang, Jian
Zhang, Junjie
Tang, Yuhai
Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
title Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
title_full Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
title_fullStr Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
title_full_unstemmed Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
title_short Regioselective S(N)2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
title_sort regioselective s(n)2' mitsunobu reaction of morita–baylis–hillman alcohols: a facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077529/
https://www.ncbi.nlm.nih.gov/pubmed/24991249
http://dx.doi.org/10.3762/bjoc.10.98
work_keys_str_mv AT xusilong regioselectivesn2mitsunobureactionofmoritabaylishillmanalcoholsafacileandstereoselectivesynthesisofaalkylidenebhydrazinoacidderivatives
AT shangjian regioselectivesn2mitsunobureactionofmoritabaylishillmanalcoholsafacileandstereoselectivesynthesisofaalkylidenebhydrazinoacidderivatives
AT zhangjunjie regioselectivesn2mitsunobureactionofmoritabaylishillmanalcoholsafacileandstereoselectivesynthesisofaalkylidenebhydrazinoacidderivatives
AT tangyuhai regioselectivesn2mitsunobureactionofmoritabaylishillmanalcoholsafacileandstereoselectivesynthesisofaalkylidenebhydrazinoacidderivatives

Ejemplares similares