Formation and cycloaddition of nonstabilized N-unsubstituted azomethine ylides from (2-azaallyl)stannanes and (2-azaallyl)silanes

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4467-4471

  Pearson, William H ^a   Clark, Roger B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; AZO COMPOUND; PYRROLIDINE DERIVATIVE; SILANE DERIVATIVE; TIN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033546247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00744-3     Document Type: Article

References (30)

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7. 2. Nonstabilized azomethine ylides are those lacking an electron withdrawing group on carbon.
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27. 9. Silyl phthalimide 4d was prepared in 35% yield from 2-methyl-l-(trimethylsilyl)-l-propanol [Hiyama, T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912-914] by conversion to the mesylate followed by displacement with potassium phthalimide. Compound 4e is commercially available.
28. 10. One general method is known for the synthesis of branched α-aminosilanes, which involves the reduction of enamines of acylsilanes, but involves the use of electrolysis conditions and large quantities of hexamethylphosphoramide (HMPA): Constantieux, T.; Picard, J.-P. Organometallics 1996, 15, 1604-1609.
29. 4, and concentrated. The crude pyrrolidines were purified by silica gel chromatography.
30. 13C NMR spectra than a stereoisomer with trans-isopropyl groups. The stereostructures of 13-18 were assigned based on NOESY experiments and similar symmetry issues.