Ontology highlight
ABSTRACT:
SUBMITTER: Jasinski M
PROVIDER: S-EPMC3388852 | biostudies-literature | 2012
REPOSITORIES: biostudies-literature
Beilstein journal of organic chemistry 20120430
An approach to enantiopure hydroxylated 2H-1,2-oxazine derivatives is presented utilizing the [3 + 3] cyclisation of lithiated alkoxyallenes and an L-erythrose-derived N-glycosyl nitrone as precursors. This key step proceeded only with moderate diastereoselectivity, but allowed entry into both enantiomeric series of the resulting 3,6-dihydro-2H-1,2-oxazines. Their enol ether double bond was then subjected to a hydroboration followed by an oxidative work-up, and finally the auxiliary was removed. ...[more]