83564-68-5Relevant academic research and scientific papers
Enantioselective synthesis of allenes by catalytic traceless petasis reactions
Jiang, Yao,Diagne, Abdallah B.,Thomson, Regan J.,Schaus, Scott E.
supporting information, p. 1998 - 2005 (2017/02/15)
Allenes are useful functional groups in synthesis as a result of their inherent chemical properties and established reactivity patterns. One property of chemical bonding renders 1,3-substituted allenes chiral, making them attractive targets for asymmetric synthesis. While there are many enantioselective methods to synthesize chiral allenes from chiral starting materials, fewer methods exist to directly synthesize enantioenriched chiral allenes from achiral precursors. We report here an asymmetric boronate addition to sulfonyl hydrazones catalyzed by chiral biphenols to access enantioenriched allenes in a traceless Petasis reaction. The resulting Mannich product from nucleophilic addition eliminates sulfinic acid, yielding a propargylic diazene that performs an alkyne walk to afford the allene. Two enantioselective approaches have been developed; alkynyl boronates add to glycolaldehyde imine to afford allylic hydroxyl allenes, and allyl boronates add to alkynyl imines to form 1,3-alkenyl allenes. In both cases, the products are obtained in high yields and enantioselectivities.
A Versatile Room-Temperature Route to Di- and Trisubstituted Allenes Using Flow-Generated Diazo Compounds
Poh, Jian-Siang,Tran, Duc N.,Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
, p. 7920 - 7923 (2015/06/30)
A copper-catalyzed coupling reaction between flow-generated unstabilized diazo compounds and terminal alkynes provides di- and trisubstituted allenes. This extremely mild and rapid transformation is highly tolerant of several functional groups. Well tolerated: A mild copper-catalyzed coupling reaction between unstabilized diazo compounds (generated in flow) and terminal alkynes is reported. The method provides di- and trisubstituted allenes with high functional-group tolerance.
A VERSATILE METHOD FOR THE PREPARATION OF ALLENIC ALCOHOLS
Keck, Gary E.,Webb, R.R.
, p. 3051 - 3054 (2007/10/02)
A convenient three step procedure to a variety of allenic alcohols is described, which relies on a highly unusual partitioning between two reaction pathways depending on the mode of addition of a reagent.
