Catalytic enantioselective alkylative aldol reaction: Efficient multicomponent assembly of dialkylzincs, allenic esters, and ketones toward highly functionalized δ-lactones with tetrasubstituted chiral centers

Journal of the American Chemical Society

Volumn 129, Issue 23, 2007, Pages 7439-7443

  Oisaki, Kounosuke ^a   Zhao, Dongbo ^a   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL REACTION; CROSSOVER; LACTONIZATION;

CATALYSIS; CHEMICAL BONDS; ENANTIOSELECTIVITY; KETONES; REACTION KINETICS;

ESTERS;

ACETOPHENONE; ALLENIC ESTER; DIALKYLZINC; DIETHYLZINC; ESTER DERIVATIVE; KETONE DERIVATIVE; LEWIS BASE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; LACTONIZATION;

ALDEHYDES; ALKYLATION; CATALYSIS; COPPER; ESTERS; KETONES; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; ZINC;

EID: 34250882833     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071512h     Document Type: Article

References (65)

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56. MS4A might shorten the lifetime of copper alkoxides in the catalytic cycle by facilitating the alkoxide ligand exchange between Cu and Zn (from IV to I in Scheme 3), thus minimizing undesired reactions catalyzed by copper alkoxides (including enolization of the ketone). MS3A, MS5A, and MS13X showed similar effects.
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58. (a) Propiophenone (14 h, 76% yield, 17% ee in the presence of HMPA) and benzalacetone (16 h, 83% yield, 35% ee in the presence of HMPA) were unsatisfactory substrates.
59. (b) At this stage, this catalytic system is not-applicable to dialkenylzincs, diarylzincs, dialkynylzincs, or monoalkylzinc halide (no reaction).
60. (a) Alexakis proposed a bridging role of the carboxylate ligand for a mixed zinc cuprate complex in a copper-catalyzed enantioselective conjugate addition. See: Alexakis, A.; Benhaim, C.; Rosset, S.; Human, M. J. Am. Chem. Soc. 2002, 124, 5262-5263.
61. Noyori also pointed out that a sulfonamide has a similar role. See: Kitamura, M.; Miki, T.; Nakano, K.; Noyori, R. Bull. Chem. Soc. Jpn. 2000, 73, 999-1014.
62. 2 produced significantly higher enantioselectivity and product yield than CuCl or CuBr. These results support a special role of the acetate ligand, which might derive from the bridging effect between copper and zinc atoms.
63. (c) The possibility that a cuprate species is the actual nucleophile in the conjugate addition cannot be excluded.
64. Copper enolate should exist under rapid equilibrium between C-enolate (C-II) and O-enolate (O-II). This equilibrium is suggested by the fact that the major diastereomer was independent of the geometry of the ketene silyl acetal in the previous copper-catalyzed aldol reaction to ketones (ref 6f), which proceeded via a copper enolate species.
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