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Pd II ‐Catalyzed Spiroketalization of Ketoallylic Diols
Author(s) -
Palmes Jean A.,
Paioti Paulo H. S.,
de Souza Leonardo Perez,
Aponick Aaron
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301723
Subject(s) - stereocenter , stereoselectivity , nucleophile , catalysis , allylic rearrangement , chemistry , anomer , carbon atom , atom (system on chip) , carbon fibers , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , ring (chemistry) , enantioselective synthesis , materials science , computer science , composite number , composite material , embedded system
A high‐yielding stereoselective method for forming spiroketals from simple ketoallylic diols is reported. Employing catalytic [PdCl 2 (MeCN) 2 ] in THF at 0 °C, these dehydrative cyclization reactions require only mild conditions to produce vinyl‐substituted spiroketals in high yields after brief reaction times with water as the only byproduct. Using this method, the stereochemical information embedded at the nucleophile is transmitted “down‐the‐chain” and efficiently sets the stereochemistry at both the anomeric carbon atom and the newly formed allylic stereocenter.