1ST DIRECT NMR SPECTROSCOPIC OBSERVATION OF A CRAM-CHELATE INVOLVING A CHIRAL ALPHA-ALKOXY ALDEHYDE

Authors
REETZ MT RAGUSE B SEITZ T
Citation
Mt. Reetz et al., 1ST DIRECT NMR SPECTROSCOPIC OBSERVATION OF A CRAM-CHELATE INVOLVING A CHIRAL ALPHA-ALKOXY ALDEHYDE, Tetrahedron, 49(38), 1993, pp. 8561-8568
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
38
Year of publication
1993
Pages
8561 - 8568
Database
ISI
SICI code
0040-4020(1993)49:38<8561:1DNSOO>2.0.ZU;2-Q
Abstract
The reaction of CH3TiCl3 with 2-benzyloxy propanal 10 at low temperatu res in CD2Cl2 leads to the formation of two diastereomeric Cram-type c helates 13a/13b which can be observed directly by C-13-NMR spectroscop y. The octahedral chelates undergo C-C bond formation with rust order kinetics, suggesting intramolecular 1,3 methyl transfer. Crossover exp eriments are unsuitable for definitive proof of intramolecularity due to ligand exchange reactions prior to Grignard-type addition.