Kinetic resolutions of azomethine imines via copper-catalyzed [3 + 2] cycloadditions

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11244-11245

  Suárez, Andrés ^a   Downey, C Wade ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZOMETHINE IMINE; COPPER; IMINE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION KINETICS; CYCLOADDITION; DIPOLE; REACTION ANALYSIS; REACTION OPTIMIZATION;

EID: 23844457533     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052876h     Document Type: Article

References (29)

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21. 3 (but not THF or EtO Ac) leads to a comparable selectivity factor. (b) CuCl and CuBr can also be used. (c) The selectivity factor is not highly temperature-dependent.
22. For a kinetic resolution that proceeds with a selectivity factor of 10. starting material of 90% ee can be obtained at 62% conversion.
23. If R (Table 2) is an acyclic alkyl group (e.g., i-Bu), the dipole decomposes to a small extent during the cycloaddition, thereby precluding a reliable determination of the selectivity factor.
24. Through X-ray crystallography, we have determined the absolute configuration of the recovered dipole from entry 2 of Table 3. The other configurations are assigned by analogy.
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