Highly diastereoselective type-I IMDA reaction forming medium-sized macrolactones.
[Structure: see text] Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.
Shin
Jeong-Taek
JT
Department of Chemistry, Hanyang University, 133-791 Seoul, South Korea.
Hong
Sung-Cho
SC
Shin
Seunghoon
S
Cho
Cheon-Gyu
CG
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D007783:Lactones; D011753:Pyrones