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A highly diastereoselective synthesis of 3-substituted isoindolin-1-one dericatives

โœ Scribed by Steven M. Allin; Christopher J. Northfield; Michael I. Page; Alexandra M.Z. Slawin

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
161 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A highly diastereoseleetive method for the synthesis of 3-substituted isoindolin-l-ones has been developed through application of a tricyclic lactam substrate as an N-acyliminium ion precursor. Ringopening of the tricyclic lactam with triethylsilane as hydride source generates the targets with up to exclusive levels of diastereoselectivity. This approach compliments that reported in the preceding paper.

๐Ÿ“œ SIMILAR VOLUMES

Highly diastereoselective synthesis and
Highly diastereoselective synthesis and template manipulation of the thiazolo[2,3-a]isoindolin-1-one ring system
โœ Steven M Allin; Darshan G Vaidya; Michael I Page; Alexandra M.Z Slawin; Tim Smit ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 130 KB

Condensation of 2-acetyl benzoic acid with L-cysteine esters proceeds with extremely high diastereoselectivity to produce the desired thiazolo[2,3-a]isoindolin-1-one products in good yield. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystallography. Stereo