Premium
Construction of Oxa‐Bridged Tetracyclic Frameworks through a Prins Bicyclic Annulation
Author(s) -
Nair Preethi N.,
Swathi Vangala,
Nishigandha Ghaytadak,
Sridhar Balasubramanian,
Reddy Jithender G,
Reddy Basi V. Subba
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801788
Subject(s) - isoindole , chemistry , annulation , bicyclic molecule , stereoselectivity , dichloromethane , stereochemistry , medicinal chemistry , organic chemistry , catalysis , solvent
A wide array of aldehydes undergo smooth cross‐coupling with 5,6‐bis(2‐hydroxyethyl)‐2‐phenyl‐3a,4,7,7a‐tetrahydro‐1 H ‐isoindole‐1,3(2 H )‐dione in the presence of 1.2 equiv. TMSOTf at –78 °C in dichloromethane to afford the corresponding hexahydro‐8a,4a‐(epoxyethano)pyrano[3,4‐ f ]isoindole‐1,3(2 H ,5 H )‐dione derivatives in good yields with excellent diastereoselectivity. This is the first report on the stereoselective construction of oxa‐bridged tetracyclic frameworks through a bicyclization strategy.