Chiral crown conformation of Rh2(S-PTTL)4: Enantioselective cyclopropanation with α-alkyl-α-diazoesters

Journal of the American Chemical Society

Volumn 131, Issue 21, 2009, Pages 7230-7231

  DeAngelis, Andrew ^a   Dmitrenko, Olga ^a   Yap, Glenn P A ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC INDUCTION; C-H INSERTION; CYCLOPROPANATION; DENSITY FUNCTIONAL THEORY CALCULATIONS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE; HYDRIDE ELIMINATION; TERT-BUTYL GROUP;

ALKYLATION; CATALYSIS; CATALYSTS; DENSITY FUNCTIONAL THEORY;

RHODIUM;

CARBOXYLIC ACID; CROWN COMPOUND; ESTER DERIVATIVE; RHODIUM TETRAACETATE; CYCLOPROPANE DERIVATIVE; DIAZONIUM COMPOUND; ESTER; ORGANOMETALLIC COMPOUND; RHODIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; CRYSTAL STRUCTURE; CYCLOPROPANATION; ENANTIOSELECTIVITY; X RAY CRYSTALLOGRAPHY; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; CYCLOPROPANES; DIAZONIUM COMPOUNDS; ESTERS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 67650523490     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9026852     Document Type: Article

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23. (a) OLYP/TZP calculations (ADF) overestimate the barrier relative to B3LYP/LANL2DZ/6-311+G(d) (Gaussian 03). However, the geometries of the transition structures were similar.
24. (b) A third, higher-energy structure, TS-3, shown in the Supporting Information, was also located and corresponds to attack on the "southern"
25. TS-2 was lower in energy than TS-1 by 1.4 kcal/mol at the OLYP/TZP level of theory; their energies were reversed (TS-1 lower by 0.3 kcal/mol) after a single-point calculation at the B3LYP/LANL2DZ/6-31G(d) level. We consider these energetic differences to be within the margin of error for these levels of theory.