Cyclic sulfamidates as precursors to alkylidene pyrrolidines and piperidines.
The reaction of the dienolate of ethyl acetoacetate (and related dienolates) with a range of 1,2- and 1,3-cyclic sulfamidates provides an entry to substituted and enantiopure alkylidenated pyrrolidines and piperidines. These heterocycles function as convenient precursors to heterocyclic beta-amino acid derivatives.
Bower
John F
JF
School of Chemistry, University of Bristol, Bristol, U.K.
Szeto
Peter
P
Gallagher
Timothy
T
D000478:Alkylation; D000586:Amination; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D006571:Heterocyclic Compounds; D010880:Piperidines; D011759:Pyrrolidines; D013457:Sulfur Compounds