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Volumn 63, Issue 51, 2007, Pages 12712-12719

Discrimination of carbonyl groups of meso-α-diketones with Horner-Wadsworth-Emmons reagent of chiral binaphthyl esters

Author keywords

[No Author keywords available]

Indexed keywords

2' ACETOXY 1,1' BINAPHTHYL DIETHOXYPHOSPHONOACETATE; 2' HYDROXY 1,1' BINAPHTHYL DIETHOXYPHOSPHONOACETATE; 8' ACETOXY 1,1' BINAPHTHYL DIMETHOXYPHOSPHONOACETATE; 8' HYDROXY 1,1' BINAPHTHYL DIMETHOXYPHOSPHONOACETATE; KETONE DERIVATIVE; MESO ALPHA DIKETONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

EID: 35748964454     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.006     Document Type: Article
Times cited : (2)

References (49)
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    • By using a chiral phosphonate reagent, Rein and co-workers successfully differentiated the diastereotopic dialdehydes and obtained the adduct with high diastereoselectivity. See:. Rein T., and Pedersen T.M. Synthesis (2002) 579-595
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    • note
    • Among the ester exchange reaction (Table 1, entries 1 and 2), the decrease of the optical purity of the methyl esters 15 and ent-16 was observed. Namely, the ee value of 15 decreased to 80% from 97% de; at the same time, that of ent-16 dropped down to 51% from 73% de of the original value. This appearance of racemization might be originated form the isomerization between the E- and Z-isomers of the adducts 11-14 and/or methyl esters 15-ent-16 during ester exchange reaction. This consideration has been experimentally supported by the photolysis of the optically pure (Z)-15 with photo-irradiation at 254 nm to give the (E)-16 without any loss of optical purity. See Ref. 10. On the other hand, no isomerization of Z-methyl ester 18 to E-methyl ester 19 occurred at all. See Ref. 17.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.