Asymmetric Diels-Alder reactions of a nitroso compound derived from D-bornane-10,2-sultam
摘要:
Acylnitroso dienophile 3 derived from D-bornane-10,2-sultam undergoes cycloaddition with high yields and complete facial selectivity to cyclopentadiene and cyclohexadiene. When the nitroso group is attached to the sultam nitrogen, it is no longer reactive in Diels-Alder reactions.
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 C-2-symmetric pyrrolidines 2d-e and camphorsultam 2f. (C) 1998 Elsevier Science Ltd. All rights reserved.