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Cascade Rearrangements Following Twofold Addition of Alkenyl Anions to Squarate Esters
Author(s) -
Paquette Leo A.
Publication year - 1998
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/(sici)1099-0690(199809)1998:9<1709::aid-ejoc1709>3.0.co;2-s
Subject(s) - chemistry , regioselectivity , reagent , asymmetric induction , chirality (physics) , cascade , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , symmetry breaking , chiral symmetry breaking , physics , quantum mechanics , chromatography , nambu–jona lasinio model
The double 1,2‐addition of alkenyl, cycloalkenyl, and alkynyllithium reagents to squarate esters constitutes a very expedient method for rapidly increasing structural complexity with formation of polycyclic end products. The simple one‐pot process is amenable to regioselective operation, stereochemical control, self‐immolative chirality transfer, 1,5‐asymmetric induction, and chemical modulation.