title: Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds.
abstract: A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a cascade of Prins/pinacol rearrangement. This method is applicable to a wide range of aldehydes such as aromatic, aliphatic, heteroaromatic, and α,β-unsaturated aldehydes.
authors.affiliation: Natural Product Chemistry, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500607, India. basireddy@iict.res.in.
authors.forename: B V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: S
authors.initials: S
authors.lastname: Gopal Reddy
authors.forename: M
authors.initials: M
authors.lastname: Ramana Reddy
authors.forename: Manika
authors.initials: M
authors.lastname: Pal Bhadra
authors.forename: A V S
authors.initials: AV
authors.lastname: Sarma
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000438:Alcohols; D000447:Aldehydes; D058116:Lewis Acids; D011714:Pyrans; D013141:Spiro Compounds