(−)-8-Amino menthol-derived perhydrobenzoxazines as chiral templates and masked aldehydes in the diastereoselective intermolecular Pauson–Khand reaction

Perhydro-1,3-benzoxazines derived from (−)-8-amino menthol behave as masked aldehydes and chiral templates in diastereoselective intramolecular Pauson–Khand reactions with norbornene and norbornadiene. The regioselectivity is excellent for unsubstituted or methyl-substituted acetylenes and moderate...

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Bibliographic Details
Published in:Tetrahedron 2012-11, Vol.68 (45), p.9293-9300
Main Authors: Maestro, Alicia, Pedrosa, Rafael, Pérez-Encabo, Alfonso, Pérez-Rueda, Juan J.
Format: Article
Language:English
Subjects:
Aldehydes
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkynes
Bonding
Chemistry
Cobalt
Cyclopentenones
Derivatives
Diastereoselective cyclization
Enantioselective synthesis
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydrolysis
Menthol
Nuclei
Organic chemistry
Pauson–Khand reaction
Preparations and properties
Terpenoids
Tetrahedrons
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Summary:Perhydro-1,3-benzoxazines derived from (−)-8-amino menthol behave as masked aldehydes and chiral templates in diastereoselective intramolecular Pauson–Khand reactions with norbornene and norbornadiene. The regioselectivity is excellent for unsubstituted or methyl-substituted acetylenes and moderate with phenyl-substituted alkynes. The stereoselection is very poor or moderate depending also on the substitution pattern of both the triple bond and the perhydrobenzoxazine nucleus. The hydrolysis of the cycloadducts leads to 2- or 3-formyl–cyclopentenone derivatives. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.08.006