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. 2014 Apr 30:10:990-5.
doi: 10.3762/bjoc.10.98. eCollection 2014.

Regioselective SN2' Mitsunobu reaction of Morita-Baylis-Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

Silong Xu  1 , Jian Shang  1 , Junjie Zhang  1 , Yuhai Tang  1
Affiliations

Regioselective SN2' Mitsunobu reaction of Morita-Baylis-Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

Silong Xu et al. Beilstein J Org Chem. .

Abstract

A highly regioselective SN2' 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.

Keywords: Mitsunobu reaction; Morita–Baylis–Hillman; SN2' reaction; azodicarboxylate; hydrazine.

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Figures

Scheme 1
Scheme 1
Synthesis of α-alkylidene-β-hydrazino acid derivatives from MBH adducts.
Scheme 2
Scheme 2
Initial investigation.
Scheme 3
Scheme 3
Synthesis of 1H-pyrazole 7.
Scheme 4
Scheme 4
A plausible mechanism for the formations of 3.
See this image and copyright information in PMC

References

    1. Licandro E, Perdicchia D. Eur J Org Chem. 2004:665–675. doi: 10.1002/ejoc.200300416. - DOI
    1. LaLonde R L, Wang Z J, Mba M, Lackner A D, Toste F D. Angew Chem, Int Ed. 2010;49:598–601. doi: 10.1002/anie.200905000. - DOI - PMC - PubMed
    1. Suzuki Y, Naoe S, Oishi S, Fujii N, Ohno H. Org Lett. 2012;14:326–329. doi: 10.1021/ol203072u. - DOI - PubMed
    1. Fernández M, Reyes E, Vicario J L, Badía D, Carrillo L. Adv Synth Catal. 2012;354:371–376. doi: 10.1002/adsc.201100722. - DOI
    1. Hashimoto T, Takiguchi Y, Maruoka K. J Am Chem Soc. 2013;135:11473–11476. doi: 10.1021/ja405444c. - DOI - PubMed