Hydroxyalkylation of conjugated nitroalkenes with activated nonenolizable carbonyl compounds

Organic Letters
Indubhusan DebIrishi N N Namboothiri

Abstract

[reaction: see text] The Morita-Baylis-Hillman reaction of a variety of conjugated nitroalkenes with activated nonenolizable carbonyl compounds such as glyoxylate, trifluoropyruvate, pyruvaldehyde, and ninhydrin in the presence of 40-100 mol % of DMAP in acetonitrile or 100 mol % of imidazole in CHCl(3) or THF provided the adducts in decent to good yields. In most cases, the reactions catalyzed by DMAP in acetonitrile were faster and provided the desired MBH adducts in higher yields as compared to the imidazole catalyzed reactions.

References

Mar 13, 2003·Chemical Reviews·Deevi BasavaiahTummanapalli Satyanarayana
Nov 25, 2003·The Journal of Organic Chemistry·P Veeraraghavan RamachandranM Venkat Ram Reddy
Feb 5, 2005·Angewandte Chemie·Varinder K AggarwalGuy C Lloyd-Jones
Oct 22, 2005·The Journal of Organic Chemistry·Go TakikawaKenji Uneyama

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Citations

Aug 20, 2015·Organic & Biomolecular Chemistry·Elumalai GopiIrishi N N Namboothiri
Jan 27, 2016·Organic & Biomolecular Chemistry·Vaijinath ManeIrishi N N Namboothiri
Mar 11, 2008·Organic & Biomolecular Chemistry·Deevi Basavaiah, Raju Jannapu Reddy
May 8, 2010·Organic & Biomolecular Chemistry·Mahiuddin BaidyaHerbert Mayr
Aug 25, 2010·Organic & Biomolecular Chemistry·Pramod ShanbhagIrishi N N Namboothiri
Jun 23, 2006·Organic & Biomolecular Chemistry·Mamta DadwalIrishi N N Namboothiri
Oct 13, 2006·Organic & Biomolecular Chemistry·Namrata RastogiIrishi N N Namboothiri
Oct 31, 2013·Organic & Biomolecular Chemistry·Xiang-Yu Chen, Song Ye
Jul 26, 2013·Organic & Biomolecular Chemistry·Xiang-Yu ChenSong Ye
Oct 5, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Wan-Yun HuangKwunmin Chen
Aug 26, 2010·Chemical Reviews·Deevi BasavaiahSatpal Singh Badsara
Nov 18, 2018·The Journal of Organic Chemistry·Kishor Chandra Bharadwaj
Apr 19, 2013·The Journal of Organic Chemistry·Rahul KumarIrishi N N Nambothiri
Jul 4, 2018·The Journal of Organic Chemistry·Lakshminarayana Satham, Irishi N N Namboothiri

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