96303-89-8Relevant articles and documents
Application in asymmetric Morita-Baylis-Hillman reactions
McIteka, Lulama P.,Lobb, Kevin A.,Kaye, Perry T.
, p. 151 - 163 (2016/10/22)
N-Substituted 2-exo-hydroxybornyl-10-sulfonamides, prepared as potential chiral auxiliaries for use in asymmetric Morita-Baylis-Hillman (MBH) reactions, have been treated with acryloyl chloride to afford the corresponding 2-exo-Acrylate esters as MBH subs
Acyclic stereoselection in the tertiary amine-catalysed addition of activated vinyl systems (Baylis-Hillman reaction) to protected chiral α-hydroxy and α-amino aldehydes
Manickum, Thavrin,Ross, Gregory H. P.
, p. 1 - 16 (2007/10/03)
The non chelation-controlled aldol-type addition of the ambident vinyl α anions derived from acrylic esters and methyl vinyl ketone to a series of protected chiral α-hydroxy and α-amino aldehydes has been investigated in order to assess some of the factors which contribute to the control of the diastereofacial selectivity.Whlist the α-methylene-β,γ-disubstituted carbonyl products showed a general preference for selectivity, some examples of syn predominance were made possible via a 'substituent tuning'approach.The observed diastereomer ratios have been interpreted in terms of the Felkin model and the Anh-Eisenstein proposals for 1,2-asymmetric induction.Simple steric effects appear to be as important as ?-orbital energies in the designation of the large 'anti group' for the application of these transition-state interpretations.Attempts to improve the overall induction via double diastereoselection approach, which combines the 1,5-induction of chiral acrylates with the 1,2-induction already present, were largely inconclusive.Methods for the routine NMR assignment of the relevant stereo-substructures have been assessed and the use of novel complementary technique is described.
ASYMMETRIC DIELS-ALDER REACTIONS: FACILE PREPARATION AND STRUCTURE OF SULFONAMIDO-ISOBORNYL ACRYLATES
Oppolzer, Wolfgang,Chapuis, Christian,Bernardinelli, Gerald
, p. 5885 - 5888 (2007/10/02)
The crystalline chiral auxiliaries 2, 3 and 4 were prepared from champhor-10-sulfonyl chlorides in 2 steps.Their readily accessible acrylates underwent efficient asymmetric Diels-Alder additions to cyclopentadiene, the topicity of wich agrees with X-ray evidence.