Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes

Journal of the American Chemical Society

Volumn 129, Issue 9, 2007, Pages 2452-2453

  Lalonde, Rebecca L ^a   Sherry, Benjamin D ^a   Kang, Eun Joo ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; GOLD DERIVATIVE; METAL COMPLEX;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

ALKADIENES; AMINATION; BENZOATES; CATALYSIS; CATIONS; GOLD; HYDROXYLATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOSPHORUS; SILVER; STEREOISOMERISM;

EID: 33847664670     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068819l     Document Type: Article

References (45)

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33. Preliminary crystallographic evidence suggests that this catalyst is polymeric in form. See Supporting Information.
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39. 31P NMR, 21.9 ppm).
40. For a preliminary crystal structure of 9, see Supporting Information.
41. 2 (94%, 98% ee). Other solvents such as MeCN (48%, 98% ee), benzene (27%, 94% ee), and THF (16%, 98% ee) gave 2 with lower yields.
42. Modifying the sulfonyl protecting group proved successful (Nosyl: 83%, 99% ee), but carbamate derivatives failed to react (Boc: <5%; Cbz: <5%).
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44. The absolute configuration of 15 was assigned by oxidative cleavage to N-p-toluenesulfonyl-L-(-)-proline methyl ester (see Supporting Information). The absolute configurations of the remaining products were assigned by analogy to 15.
45. See Supporting Information for a representative deprotection procedure.