Chiral lithium amides on solid support: Synthesis and applications in enantioselective deprotonation of cyclic ketones

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8755-8758

  Majewski, Marek ^a   Ulaczyk, Agnieszka ^a   Wang, Fan ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Amines; Deprotonation; Enantioselection; Polymer support

Indexed keywords

AMIDE; KETONE DERIVATIVE; ORGANOLITHIUM COMPOUND; POLYMER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0033544830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01882-1     Document Type: Article

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15. R axial proton of tropinone selectively.
16. 2 for 2 days. The amine loading was established by elemental analysis. Before deprotonation, the amines were swollen in THF (rt, 30 min). Amide formation with BuLi (1 mmol per mmol of amine, 0°C, 3 h) was followed by deprotonation (0.8 mmol ketone, 78°C, overnight) and electrophile (0.8 mmol).
17. This work was supported by a grant from the National Science and Engineering Research Council of Canada.