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Volumn 55, Issue 29, 1999, Pages 8869-8882

Catalytic, enantioselective alkylations of N,O- and N,N-acetals and hemiacetals

Author keywords

Acetals; Amino Acids; Asymmetric Synthesis; Copper

Indexed keywords

3 (BENZOYL) 2 (ACETAMINO)PROPANOIC ACID ETHYL ESTER; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033575447     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00450-0     Document Type: Conference Paper
Times cited : (45)

References (43)
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    • Our recent work has focused on the use of chiral, transition metalphosphine complexes to catalyze the addition of carbon based nucleophiles to imino esters (X = Ts) with high diastereo- and enantioselcctivity to yield protected amino acids S: (a) Ferraris, D.; Young, B. Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
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    • The drawbacks of this synthetic methodology are the purification and hydrolytic lability of the imino 3 as well as the deprotection of the tosyl group after alkylation
    • (c) Drury, W. J. III, Ferraris, D.; Cox, C.; Young, B.; Lectka, T. J. Am. Chem. Sec. 1998. 120, 11006-11007. The drawbacks of this synthetic methodology are the purification and hydrolytic lability of the imino 3 as well as the deprotection of the tosyl group after alkylation.
    • (1998) J. Am. Chem. Sec. , vol.120 , pp. 11006-11007
    • Drury W.J. III1    Ferraris, D.2    Cox, C.3    Young, B.4    Lectka, T.5
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    • This reaction was not of interest to us and for this reason, the yields and selectivities were not optimized. For catalytic enantioselective alkylations of ethyl glyoxylate, see: (a) Evans, D. A.; Olhava, E. J.; Johnson, J. S.; Janey, J. M. Angew. Chem. Int. Ed. Eng. 1998, 37, 3372.
    • (1998) Angew. Chem. Int. Ed. Eng. , vol.37 , pp. 3372
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    • All deprotection products a were converted to (L)-benzoylalanine upon acidic hydrolysis. The hydrolysis products were identical in every way to the literature compound, see: Gulobev, A. S.; Sewald, N.; Burger, K. Tetrahedron 1996, 52, 14757-14776.
    • (1996) Tetrahedron , vol.52 , pp. 14757-14776
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    • For acid catalyzed siloxane formation, see: Grubb, W. T. J. Am. Chem. Soc. 1954, 76, 3408-3414.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 3408-3414
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    • The optical purity of compound was obtained by the use of chiral shift reagent preseodymium tris[3-(heptafluoropropylhdroxymethylene)-(+)-camphorale see: Parker, D. Chem. Rev. 1991, 1441-1457.
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    • Parker, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.