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Novel regioselective synthesis of decahydrobenzocarbazoles using rhodium generated carbonyl ylides with indoles

โœ Scribed by Sengodagounder Muthusamy; Chidambaram Gunanathan; Srinivasarao Arulananda Babu

Book ID
104211534
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
74 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Intermolecular cycloadditions of five-membered cyclic carbonyl ylides 3 with indole, N-methylindole and N-benzylindole afforded decahydrobenzo[c]carbazole 4a-f or decahydrocyclopenta[c]carbazole 4g-h derivatives with high regioselectivity.

With N-benzoylindole and N-sulphonylindole, decahydrobenzo[c]carbazoles 4i,j and the regioisomer decahydrobenzo[a]carbazoles 5i,j are isolated. The electron withdrawing substituent reduces both regioselectivity and reactivity of the cycloadditions. This methodology generated oxa-bridged (unnatural) decahydrobenzocarbazole derivatives with complete control of four stereocenters.

๐Ÿ“œ SIMILAR VOLUMES

Novel chemoselective 1,3-dipolar cycload
Novel chemoselective 1,3-dipolar cycloaddition of rhodium generated carbonyl ylides with arylidenetetralones
โœ Sengodagounder Muthusamy; Srinivasarao Arulananda Babu; Chidambaram Gunanathan ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 70 KB

Treatment of various a-diazo ketones 1 and arylidenetetralones 2 in the presence of rhodium(II) acetate dimer leads to spiro-dioxa ring systems 3 as the only C O addition products with high regio-and chemoselectivity.