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( R/S )‐BINOL‐α‐Phosphoryloxy Enecarbamate‐Mediated and ( R / S )‐Titanium(IV) BINOLates‐Catalyzed Enantioselective Intramolecular Heck/Aza‐Diels–Alder Cycloaddition (IHADA): An Expedient Methodology
Author(s) -
Khan Imran A.,
Saxena Anil K.
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300522
Subject(s) - enantioselective synthesis , chemistry , intramolecular force , cycloaddition , titanium , catalysis , combinatorial chemistry , heck reaction , stereochemistry , organic chemistry , palladium
An ( R/S )‐titanium(IV) BINOLate‐catalyzed highly enantioselective intramolecular Heck/aza‐Diels–Alder cycloaddition (IHADA) cascade was developed to prepare tetrahydropyridoindoles (tHPs) and octahydropyrazinopyridoindoles (oHPPs) from in situ generated ( R / S )‐BINOL α‐phosphoryloxy carbamate ( αPPC2 ) in one pot. Chiral cooperativity between ( R / S )‐αPPC2 and ( R / S )‐titanium(IV) BINOLate was observed and successfully utilized for the construction of various tHPs (7 examples) and oHPPs (17 examples).