Synthetic Access to All Four Stereoisomers of Oxetin.
A short synthesis of all four stereoisomers of 3-amino-2-oxetanecarboxylic acid (oxetin) is described. The oxetane core is built using a Paternò-Büchi photochemical [2 + 2] cycloaddition; from the key intermediates, complementary resolution protocols provide access to enantiomerically pure oxetin and epi-oxetin on gram-scale.
Ahmad F
AF
Kassir
Photochemistry Department, Chemical Industries Research Division, National Research Center , Dokki, 12622 Giza, Egypt.
Sherif S
SS
Ragab
Thao A M
TA
Nguyen
Florence
F
Charnay-Pouget
Régis
R
Guillot
Marie-Christine
MC
Scherrmann
Thomas
T
Boddaert
David J
DJ
Aitken
D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism
D004988:Ethers, Cyclic; C043272:oxetin