Gold-catalyzed [4C+2C] cycloadditions of allenedienes, including an enantioselective version with new phosphoramidite-based catalysts: Mechanistic aspects of the divergence between [4C+3C] and [4C+2C] pathways

Journal of the American Chemical Society

Volumn 131, Issue 36, 2009, Pages 13020-13030

  Alonso, Isaac ^a   Trillo, Beatriz ^a   López, Fernando ^c   Montserrat, Sergi ^b   Ujaque, Gregori ^b   Castedo, Luis ^a   Lledós, Agustí ^b   Mascareñas, Jose L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; CYCLOADDITIONS; CYCLOADDUCTS; ELECTRON-ACCEPTOR LIGANDS; ENANTIOSELECTIVE; GOLD CATALYSTS; GOOD YIELD; MECHANISTIC ASPECTS; PHOSPHORAMIDITES; RING CONTRACTION; STEREO-SELECTIVE;

CATALYSIS; CATALYSTS; DYES; ENANTIOSELECTIVITY; GOLD; GOLD COMPOUNDS;

CYCLOADDITION;

ALKADIENE; ALKYL GROUP; ALLENE DERIVATIVE; CARBENE; CATION; GOLD; PHOSPHORAMIDOUS ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CYCLOADDITION; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 70349159148     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905415r     Document Type: Article

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93. Comparison of optical rotations and chiral HPLC analysis allow to propose the same absolute configuration for the remaining [4C+2C] adducts obtained with (S,S,S)-I. Catalyst (R,R,R)-K provided, in every case, opposite absolute configuration than (S,S,S)-I.
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98. Reaction of allenediene 1a with catalyst B (10 mol %), in the presence of 3 equiv of MeOH, provided the same ratio of [4C+3C] and [4C+2C] products as obtained in the absence of MeOH (2a:3a ratio = 1:10).
99. In consonance with this proposal, Toste et. al. reported that a related allenediene selectively mono deuterated at the terminal position of the diene provided a stereoselective [4C+2C] cycloaddition, making very unlikely a cationic pathway involving species such as II (see ref 11).
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105. The 1,2-H shift leading to V is actually a two step process: the first one with a 8.6 kcal/mol activation barrier corresponds to an axial-to-ecuatorial conformational change on the seven-membered ring to obtain the appropriate parallel disposition of the orbitals implicated in the subsequent 1,2-H shift; this intermediate, IV′, lies 8.1 kcal/mol over IV. The second step is the 1,2-H shift properly speaking with an activation barrier of 2.2 kcal/mol. The energy barrier for the transformation of IV′ to IV is so small (0.5 kcal/mol), that in practice, the evolution from intermediate IV to the product V can be considered taking place in a single step. Thus, for clarity reasons, we depicted this process in Figure 4 as a single step with the overall barrier of 10.3 kcal mol. For a complete description of this process, see the Supporting Information.
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