Probing the mechanism of Prins cyclisations and application to the synthesis of 4-hydroxytetrahydropyrans.
Trapping intermediates on the Prins cyclisation pathway with carbon-based nucleophiles has given further insight into factors affecting the acid-mediated reactions of homoallylic alcohols with aldehydes, enabling the design of efficient syntheses of 4-hydroxy-2,6-disubstituted tetrahydropyrans.
Barry
Conor S
CS
School of Chemistry, University of Bristol, Cantock's Close, Bristol, UKBS8 1TS. chris.willis@bristol.ac.uk.
Bushby
Nick
N
Harding
John R
JR
Hughes
Rachael A
RA
Parker
Gregory D
GD
Roe
Richard
R
Willis
Christine L
CL
D000080:Acetals / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D002396:Catechols / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure
D000080:Acetals; D000438:Alcohols; D002396:Catechols; D003486:Cyanides; D006571:Heterocyclic Compounds; D006859:Hydrogen