( 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 | Zendy

Khan Imran A. | Zendy; Saxena Anil K. | Zendy

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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).

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