2-Phospha[3]ferrocenophanes with planar chirality: Synthesis and use in enantioselective organocatalytic [3 + 2] cyclizations

Journal of the American Chemical Society

Volumn 130, Issue 43, 2008, Pages 14030-14031

  Voituriez, Arnaud ^a   Panossian, Armen ^a   Fleury Brégeot, Nicolas ^a   Retailleau, Pascal ^a   Marinetti, Angela ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE DERIVATIVE; FERROCENE DERIVATIVE; FUMARIC ACID; KETONE DERIVATIVE; PHOSPHINE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYST; CHIRALITY; CYCLIZATION; CYCLOADDITION; ENANTIOMER; ENANTIOSELECTIVITY; SOLID STATE; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOPENTANES; ESTERS; IRON COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 54849416798     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806060a     Document Type: Article

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35. The lower reactivities of 5a and 5b, compared to that of 5c, can be tentatively ascribed to a lower nucleophilic character for 5a and to an increased steric hindrance for 5b.
36. In analogous conditions phosphine 5a afforded 8a in 11% ee, while 5b gave a 12% ee for reactions run at 90°C.
37. The catalyst amount can be reduced, while retaining a significant catalytic activity and the same levels of enantiocontrol: for reaction in entry 5, conversion rates of 74% and 40% were observed after 40 h at rt, at catalysts amounts of 5% and 1% respectively (96% ee).
38. For preliminary considerations on the sense of asymmetric induction and a model for the phosphine-allene adduct, see Supporting Information.
39. 11CH=CHCOPh.