128252-46-0Relevant academic research and scientific papers
New acylnitroso compounds for the asymmetric oxyamination of dienes
Gouverneur,McCarthy,Mineur,Belotti,Dive,Ghosez
, p. 10537 - 10554 (2007/10/03)
A series of new enantiomerically pure acylnitroso compounds have been prepared and tested as dienophiles for the asymmetric oxyamination of dienes. Very high selectivities were obtained with acylnitroso compounds derived from diphenylmethoxymethyl pyrrolidine 2c, the C2-symmetric pyrrolidines 2d-e and camphorsultam 2f.
Asymmetric Diels-Alder Cycloadditions with Chiral Carbamoyl Dienophiles
Defoin, Albert,Brouillard-Poichet, Agnes,Streith, Jacques
, p. 109 - 123 (2007/10/02)
Chiral acylnitroso dienophiles 14, which were obtained from L-proline and from D-mandelic acid, reacted with cyclohexa-1,3-diene to give the expected diastereoisomers 15 and 16 (Scheme 2 and Table 1).The d.e. values for these Diels-Alder reactions were moderate; they are related to the molecular stiffness of the dienophiles.The absolute configuration of the major cycloadducts was interpreted in terms of HOMO/LUMO interactions, the approach being 'endo' and the acylnitroso dienophiles reacting from their s-cis-conformation.
Asymmetric Diels-Alder cycloadditions with acylnitroso dienophiles obtained from L-proline
Brouillard-Poichet,Defoin,Streith
, p. 7061 - 7064 (2007/10/02)
N-acylnitroso derivatives of L-proline were formed in situ from the corresponding hydroxamic acids. They reacted easily with 1,3-cyclohexadiene to give the corresponding diastereoisomeric pairs of Diels-Alder cycloadducts with d.e. values ranging from 52 to 68%.
