Metalation-alkylation of N-activated pyrrolidines. Rigorous proof of retention for both steps

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6764-6765

  Kopach, Michael E ^a   Meyers, A I ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029822037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961272g     Document Type: Article

References (38)

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28. Determined by X-ray single crystal analysis (see ref 6).
29. 13C NMR assignments were made with the assistance of 500 MHz HMQC. Details are provided in the supporting information.
30. C bridgehead methine.
31. C.
32. D) was estimated to be 20-21 (Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper Row: New York, 1987; p 234).
33. In order for the alkylation reaction to proceed with high de it was necessary to use diethyl ether as the solvent. Substituting THF as solvent results in a 1:1 α/β selectivity even at -90°C.
34. Competitive alkylation at C19 was not observed under any conditions. Presumably this is due to the inaccessibility of both methylene protons at C19 from the bulk of the adjacent neopentyl center.
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36. 18
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