Morita-Baylis-Hillman reaction, reviews

Limberakis, C. Morita-Baylis-Hillman reaction. In Name Reactions for Homologa-tions-Part I Li, J. J., Corey, E. J., Eds. Wiley Sons Hoboken, NJ, 2009, pp 350-380. (Review). 

Recent advances in organocatalytic asymmetric Morita-Baylis-Hillman reactions and their aza-variants have been reviewed (112 references), with a particular focus on amine- and phosphine-catalysed routes, and bifunctional catalysis. 0... 

Review of Morita-Baylis-Hillman reaction for the asymmetric synthesis (a) Langer, P. (2000) Ange-waruite Chemie International Edition in ng h 39, 3049-52. 

A new tandem Michael-aldol reaction of a,ft-unsaturated compounds bearing a chalcogenide or thioamide group with electrophiles has been reviewed.163 The product o -(o -hydroxyalkyl)enones - Morita-Baylis-Hillman (MBH) adducts - can be formed with significant stereocontrol when an optically active thione is used. 

A review on ynolates, including the synthesis of p-lactones, has appeared <03S2275>. Morita-Baylis-Hillman-type adducts have been converted into a-alkylidene-p-lactones 65, which on reaction with dimethyltitanocene can be transformed into 3-alkylidene-2-methyleneoxetanes <03OL399>. Lactones 66 have been obtained via the cinchona alkaloid-catalyzed dimerization of monosubstituted ketenes <03OL4745>. The PdCh-promoted synthesis of P-lactones 67 have been achieved via cyclocarbonylation of 2-alkynols <03OL4429>. 

Abstract The organocatalytic asymmetric Mannich reaction and the related aza-Morita-Baylis-Hillman have been reviewed. The activities in this field have been snbdivided based on the types of catalysts that have been ntilized, which includes catalysis by enamine-forming chiral amines, chiral Br0nsted bases, chiral Brpnsted acids, and phase-transfer catalysts. 

A phosphine sulfonamide derived from L-threonine promotes aza-Morita-Baylis-Hillman (aza-MBH) reactions of sulfinylimines in up to 96% yield and 97% ee. A review describes the synthesis of chiral amines under mild conditions via catalytic asymmetric aza-MBH reactions. Proline/DABCO (l,4-diazabicyclo[2.2.2]octane) co-catalysis of enantioselective aza-MBH reactions gives good to high yields and up to 99%... 

The reactivity of activated C-C double bonds with NHC has been reviewed more specifically. This report details the umpolung reaction involving Michael acceptors, the use of carbenes in Morita-Baylis-Hillman as well as in various cycloadditions. The catalysis of alkyne cycloaddition with nitrile oxide is also covered. 

A review of the Morita-Baylis-Hillman (MBH) reaction has covered mechanism, activated olefins and electrophiles as substrates, multicomponent and intramolecular reactions, and the use of ionic liquid reaction media. ... 

This chapter reviews our study of Morita-Baylis-Hillman (MBH) and vinylmel ation reactions for the synthesis of achiral and chiral, functionalized, fluorinated allyl alcohols. Vinylmetalation of fluoro-carbonyls with aluminum and copper reajgents for the synthesis of unsubstituted, and p-substituted fluorinated allyl alcohols is summarized. An exploratory study of terpenyl alcohols as chiral auxiliaries in these reactions is also discussed. 

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