Stereoselective Syntheses of Protected Amino-hydroxy-cyclopentane-carbaldehyde Derivatives from 7-Oxabicyclo[2.2.1]hept-5-en-2-yl Systems | Zendy

JeanLouis Reymond | Zendy; Pierre Vogel | Zendy

Open Access

Stereoselective Syntheses of Protected Amino-hydroxy-cyclopentane-carbaldehyde Derivatives from 7-Oxabicyclo[2.2.1]hept-5-en-2-yl Systems

Author(s) -

JeanLouis Reymond,

Pierre Vogel

Publication year - 1990

Publication title -

chimia international journal for chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.387

H-Index - 55

eISSN - 2673-2424

pISSN - 0009-4293

DOI - 10.2533/chimia.1990.342

Subject(s) - cyclopentane , chemistry , stereoselectivity , cycloaddition , double bond , stereochemistry , alkyl , medicinal chemistry , catalysis , organic chemistry

Cycloaddition of azido formates to the double bond of 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives gave mixtures of triazolines that could be separated by chromatography. Their acid-catalyzed dediazoniations generate 7-oxabicyclo[2.2.1]hept-2-yl cation intermediates that rearrange into the corresponding more stable 2-oxabicyclo[2.2.1]hept-3-yl cation intermediates which are quenched externally or internally to give products that are protected amino-hydroxy-cyclopentane-carbaldehyde derivatives, with high stereoselectivity. The migratory aptitude of an alkyl group (e.g. ? bond C(1)–C(6) in 5-oxo-7-oxabicyclo[2.2.1]hept-2-yl cation intermediates) is significantly lower than that of the acyl group (e.g. ? bond C(1)–C(6) in 6-oxo-7-oxabicyclo[2.2.1]hept-2-yl cation intermediates) in pinacolic rearrangements.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research