title: Synthesis of oxaspirannic building blocks by regioselective nitroso-Diels-Alder reactions.
abstract: Spirocyclic structures: Nitroso-Diels-Alder reactions of 1,3-disubstituted cyclohexadienes were found to be regiodivergent, depending on the nitroso derivative used. Cycloaddition with Wightman's chloronitroso derivative was totally regio- and stereoselective. This methodology was applied to the synthesis of heterospiranic frameworks after N-O bond cleavage and cyclization (see scheme; Boc=tert-butoxycarbonyl, Tf=trifluoromethanesulfonyl).
authors.affiliation: Institut de Chimie Moléculaire et des Matériaux d'Orsay, Université de Paris-Sud, Orsay, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Sancibrao
authors.forename: Didier
authors.initials: D
authors.lastname: Gori
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky
authors.forename: Guillaume
authors.initials: G
authors.lastname: Vincent
mesh_terms: D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D009603:Nitroso Compounds; D013141:Spiro Compounds