Iterative stereospecific reagent-controlled homologation using a functionalized α-chloroalkyllithium: Synthesis of cyclic targets related to epibatidine

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1318-1321

  Emerson, Christopher R ^a   Zakharov, Lev N ^a   Blakemore, Paul R ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952605203     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103170y     Document Type: Article

References (42)

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37. Incomplete α-deuteration of the starting material used for entries 3 and 4, together with the expected faster H transfer from the minor H- 12 components, accounts in part for the generation of 14 as a mixture of all three (HH, HD, and DD) isotopomers. β-Elimination of HCl from 8a by the action of another 8a as base provides a second mechanism for proton transfer that could lead to HD- 14 from D- 12, see ref.
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