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The generation and cycloaddition of 2-azaallyl anions and azomethine ylides from a common precursor. A novel synthesis of indolizidines and other heterocycles

โœ Scribed by William H. Pearson; Yuan Mi

Book ID
104257572
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
228 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Nonstabilized azomethine ylides may be generated by the intra-or intermolecular N-alkylation of 2-(azaallyl)stannanes or 2-(azaallyl)silanes. The cycloaddition of these ylides with electron poor or electron rich dipolarophiles provides indolizidines or simple monocyclic pyrrolidines (e.g., 5 --~ 8 --~ 9 --~ 10). The same 2-(azaallyl)stannanes may be subjected to tin-lithium exchange to afford 2-azaallyl anions, which may also enter into cycloadditions (e.g., 11 --~ 12 or 13). An in situ method for the generation and cycloaddition of azomethine ylides from an t.o-halocarbonyl compound, an oc-stannyl amine, and a dipolarophile is also described (Table 2).

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: The Generation and
ChemInform Abstract: The Generation and Cycloaddition of 2-Azaallyl Anions and Azomethine Ylides from a Common Precursor. A Novel Synthesis of Indolizidines and Other Heterocycles.
โœ W. H. PEARSON; Y. MI ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 32 KB ๐Ÿ‘ 2 views

The Generation and Cycloaddition of 2-Azaallyl Anions and Azomethine Ylides from a Common Precursor. A Novel Synthesis of Indolizidines and Other Heterocycles. -Inter-or intramolecular N-alkylation of (azaallyl)stannanes or -silanes generates nonstabilized azomethine analogues which undergo cycloa

Transmetallation of n-(trialkylstannyl)m
Transmetallation of n-(trialkylstannyl)methylimines. A new method for the generation and cycloaddition of 2-azaallyl anions.
โœ William H. Pearson; Daniel P. Szura; William G. Harter ๐Ÿ“‚ Article ๐Ÿ“… 1988 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 219 KB

Transmetallation of imines 1 at -78' with RLi provided 2-azaallyl anions 2, which readily undergo cycloaddition with olefinic anionophiles, providing pyrrolidines. Of particular note is the generation of unstabilized 2-azaallyl anions for the first time (Table 1, entries l-3).