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Volumn 9, Issue 24, 2011, Pages 8437-8444

Thiazolium-catalyzed intermolecular Stetter reaction of linear and cyclic alkyl α-diketones

Author keywords

[No Author keywords available]

Indexed keywords

ACYL ANIONS; ANION ADDITION; BIACETYL; CHALCONES; CONJUGATE ADDITION; DIKETONES; MECHANISTIC ASPECTS; MICROWAVE DIELECTRIC HEATING; N-HETEROCYCLIC CARBENES; STETTER REACTION; UMPOLUNG;

EID: 84857550600     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob06480k     Document Type: Article
Times cited : (23)

References (53)
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    • In general, known classes of acyl anion sources are aldehydes, pyruvates, acylsilanes, and benzoins themselves. Very recently, the umpolung reactivity of Michael acceptors has also been reported
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    • Acetyldimethylphenylsilane is also commercially available from Olymchemical Ltd (Chunquan Rd. Pudong, Shanghai, 201203-People's Republic of China) As previously observed (see ref. 7b), the use of catalytic thiamine-hydrochloride 3 (20 mol%) resulted in a sluggish nucleophilic addition The stereoelectronic preference for thiazolium-derived carbenes (in contrast to triazolium or imidazolium derived carbenes) has been observed several times when alkyl acyl anion equivalents are used. For a discussion on this topic, see
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    • Ref. 8a,c and 11. The stereoelectronic differences between thiazolium, triazolium and imidazolium derived carbenes have recently been reviewed
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    • In a similar vein, the asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates reported by Rovis and co-workers produces α-ketoamide products, which can be further functionalized to give useful intermediates.
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    • The assignment of the relative stereochemistry of bicyclo 12 and its enantioselective synthesis are currently under investigation in our laboratories and they will be the object of a forthcoming publication For the asymmetric Lewis base-catalyzed domino Michael/aldol reaction of 1,2-cyclohexanedione with α,β-unsaturated aldehydes, see Ref. 2d
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.