Selective vinyl C-H lithiation of cis-stilbenes

Journal of the American Chemical Society

Volumn 131, Issue 9, 2009, Pages 3142-3143

  Tricotet, Thomas ^a   Fleming, Patricia ^a   Cotter, Juliet ^a   Hogan, Anne Marie L ^a   Strohmann, Carsten ^b   Gessner, Viktoria H ^b   O'Shea, Donal F ^a  

^a University College Dublin   (Ireland)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OLEFINS;

CARBOLITHIATION; COMPUTATIONAL STUDIES; HETEROCYCLES; LITHIATION; REGIO-SELECTIVE; STEREO-SELECTIVE;

STEREOCHEMISTRY;

CIS STILBENE DERIVATIVE; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; LITHIUM; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; LITHIATION; STEREOCHEMISTRY; X RAY DIFFRACTION; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; LITHIUM; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STILBENES;

EID: 77958519900     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja809941n     Document Type: Article

References (14)

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11. 8 at-15 °C identified (E)-3a as the major component (SI).
12. Lithiation of 4d with BuLi alone gave the CIPE controlled ortho-lithiation.
13. For a related reaction in which alkene lithiation was achieved with LDA, THF,-30 to 0 °C when the ortho position was blocked by TMS substitution, see: Reed, M. A.; Chang, M. T.; Snieckus, V. Org. Lett. 2004, 6, 2297.
14. E2ret mechanism which may not be the case for all electrophiles.