89104-23-4Relevant academic research and scientific papers
A Four-Component Reaction for the Synthesis of Dioxadiazaborocines
Flagstad, Thomas,Petersen, Mette T.,Nielsen, Thomas E.
, p. 8395 - 8397 (2015)
A four-component reaction for the synthesis of heterocyclic boronates is reported. Readily available hydrazides, α-hydroxy aldehydes, and two orthogonally reactive boronic acids are combined in a single step to give structurally distinct bicyclic boronates, termed dioxadiazaborocines (DODA borocines). In this remarkable process, one boronic acid reacts as a carbon nucleophile and the other as a boron electrophile to provide enantio- and diastereomerically pure heterocyclic boronates with multiple stereocenters in high yields.
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.
Diastereoselective synthesis of protected 2,3-dihydroxynitriles from 2- hydroxy acids
Hutin, Pierre,Larchevêque, Marc
, p. 220 - 222 (2007/10/03)
The DIBAL-H reduction of dioxolanones 2 prepared from 2-hydroxy acids followed by addition of acetone cyanohydrin affords the syn 2,3- dihydroxynitriles in high enantiomerical purities.
OPTICAL ACTIVITY OF LACTONES AND LACTAMS-I; CONFORMATIONAL DEPENDENCE OF THE CIRCULAR DICHROISM OF 1,3-DIOXOLAN-4-ONES
Polonski, T.
, p. 3131 - 3137 (2007/10/02)
Several optically active 1,3-dioxolan-4-ones were synthesized from corresponding α-hydroxy acids.The Cotton effect sign of these compounds can be explained by Weigans's sector rules.The existence of an equilibrium between envelope and planar conformations
