Diastereoselective aziridination of 2-B(pin)-substituted allylic alcohols: an efficient approach to novel organoboron compounds.
We report that 2-B(pin)-substituted allylic alcohols are good substrates for diastereoselective aziridinations in the presence of PhI(OAc)(2) and N-aminophthalimide. Under the aziridination conditions, the valuable B-C bond remains intact, affording a variety of novel boron-substituted aziridines in good yields and excellent diastereoselectivities. Oxidation of the aziridine B-C bond enables generation of syn-1,3-aminohydroxy-2-ketones with high diastereoselectivity.
P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Department of Chemistry, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Jorge
J
Hernández-Toribio
Mahmud M
MM
Hussain
Kevin
K
Cheng
Patrick J
PJ
Carroll
Patrick J
PJ
Walsh
D001388:Aziridines / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D001388:Aziridines; D001896:Boron Compounds; D007659:Ketones; D020005:Propanols; C006463:allyl alcohol; C033132:aziridine