Related Experiment Video
Updated: Aug 12, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines
Brian A Lanman1, Andrew G Myers
1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Abstract:
[reaction: see text] Enantio- and diastereoselective syntheses of trans-2,5-disubstituted morpholine derivatives are described. The routes are initiated by the reaction of enantiopure epoxides (2) with amino alcohols (3) and address the problem of regioselective hydroxyl activation-ring closure of the resulting amino diol adducts for (amino alcohol-derived) alkyl substituents of different steric demands.
More Related Videos
Related Concept Videos
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stereoisomerism of Cyclic Compounds
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

