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Volumn , Issue 19, 2011, Pages 3430-3436

A tandem isomerization-Mannich reaction for the enantioselective synthesis of β-amino ketones and β-amino alcohols with applications as key intermediates for ent-nikkomycins and ent-funebrine

Author keywords

Allylic compounds; Amino alcohols; Amino ketones; Mannich reaction; Natural products

Indexed keywords


EID: 79959697123     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100352     Document Type: Article
Times cited : (24)

References (67)
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    • For clarity and consistency, in Scheme 1 only the derivatives with the (S) absolute configuration at the sulfur stereocenter are indicated because these compounds are used later in corresponding asymmetric syntheses.
    • For clarity and consistency, in Scheme 1 only the derivatives with the (S) absolute configuration at the sulfur stereocenter are indicated because these compounds are used later in corresponding asymmetric syntheses.
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    • 1. Aryl ketones, such as 5b and 6b, are more stable, whereas alkyl derivatives are less stable. For instance, the more sensitive β-amino ketone 5a gives a small amount of epimerization/ decomposition (around 4 %) during deprotection.
    • 1. Aryl ketones, such as 5b and 6b, are more stable, whereas alkyl derivatives are less stable. For instance, the more sensitive β-amino ketone 5a gives a small amount of epimerization/ decomposition (around 4 %) during deprotection.
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    • s) sulfinimine to afford the other stereoisomer, which is not consistent with our experimental results.
    • s) sulfinimine to afford the other stereoisomer, which is not consistent with our experimental results.
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    • Reactions via the cis isomer of the sulfinyl imine have been proposed to explain the stereoselectivity during reactions with cyclohexadienyl Grignard reagents, see:, however, to the best of our knowledge, there is no evidence to date for a possible trans-cis isomerization with these N-tert-butanesulfinyl imines.
    • Reactions via the cis isomer of the sulfinyl imine have been proposed to explain the stereoselectivity during reactions with cyclohexadienyl Grignard reagents, see:, M. S. Maji, R. Fröhlich, A. Studer, Org. Lett. 2008, 10, 1847-1850 however, to the best of our knowledge, there is no evidence to date for a possible trans-cis isomerization with these N-tert-butanesulfinyl imines.
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    • CCDC-802575 (for 12a), -CCDC-802578 (for 11c), -CCDC-802576 (for 7d), and -CCDC-802577 (for 11d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.