Mukherjee Munmun, Zhou Yubai, Dai Yijing, Gupta AniL K, Pulgam V Reddy, Staples Richard J, Wulff William D
Department of Chemistry, Michigan State University, East Lansing, MI, 48824, USA.
Chemistry. 2017 Feb 21;23(11):2552-2556. doi: 10.1002/chem.201605955. Epub 2017 Jan 27.
A highly diastereoselective and enantioselective method for the multicomponent aziridination of chiral aldehydes has been developed with BOROX catalysts of the VANOL (3,3'-diphenyl-2,2'-bi-1-naphthol) and VAPOL (2,2'-diphenyl-(4-biphenanthrol)) ligands. Very high to perfect catalyst control is observed with most all substrates examined including aldehydes with chiral centers in the α- and β-positions. High catalyst control was also observed for a number of chiral heterocyclic aldehydes allowing for the preparation of epoxy aziridines, bis(aziridines) and ethylene diaziridines. Application of this reaction in the synthesis of β -homo-d-alloisoleucine and β -homo-l-isoleucine is reported.
已开发出一种使用VANOL（3,3'-二苯基-2,2'-联-1-萘酚）和VAPOL（2,2'-二苯基-(4-联菲罗啉)）配体的BOROX催化剂对手性醛进行多组分氮杂环丙烷化反应的高度非对映选择性和对映选择性方法。在所研究的大多数底物中，包括在α和β位具有手性中心的醛，都观察到了非常高甚至完美的催化剂控制效果。对于许多手性杂环醛也观察到了高催化剂控制效果，从而能够制备环氧氮杂环丙烷、双（氮杂环丙烷）和乙二氮杂环丙烷。报道了该反应在β-高-D-别异亮氨酸和β-高-L-异亮氨酸合成中的应用。
