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Volumn 47, Issue 21, 2008, Pages 3979-3983

Catalytic synthesis of β3-amino acid derivatives from α-amino acids

Author keywords

Amino acids; Carbonylation; Cobalt; Insertion reactions; Ring expansion

Indexed keywords

AMINATION; AMINO ACIDS; CARBONYLATION; CHEMICAL REACTIONS; NITROGEN COMPOUNDS; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

EID: 47049104390     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705310     Document Type: Article
Times cited : (26)

References (72)
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    • For reviews on the medicinal uses of β-amino acids, see: a) T. C. Boge, G. I. Georg in ref. [1a], pp. 1-43;
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    • See Supporting Information
    • See Supporting Information.
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    • 4] has been reported: a) R. J. Klingler, J. W. Rathke, J. Am. Chem. Soc. 1994, 116, 4772-4785;
    • 4] has been reported: a) R. J. Klingler, J. W. Rathke, J. Am. Chem. Soc. 1994, 116, 4772-4785;
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    • 8] is well documented: J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Sausalito, 1987.
    • 8] is well documented: J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Sausalito, 1987.
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    • The solvent effects, when using 1/BnOH as the catalyst, followed the trends in Table 1. Therefore, DME was used in subsequent reactions.
    • The solvent effects, when using 1/BnOH as the catalyst, followed the trends in Table 1. Therefore, DME was used in subsequent reactions.
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    • The absolute configuration at the 4-position is retained, though its assignment has changed due to the change in priority from oxygen to carbon
    • The absolute configuration at the 4-position is retained, though its assignment has changed due to the change in priority from oxygen to carbon.
  • 68
    • 53549102303 scopus 로고    scopus 로고
    • Carbonylation of 2h using 5 mol% 1/BnOH for 6 h yielded 37% oxazinone 3h. Longer reaction time (24 h) and higher catalyst loading (10 mol%) left no signs of either oxazoline 2h or oxazinone 3h, but gave exclusively 2-(4-tert-butylphenyl)-4-ethyl-2-oxazalone. For details, see C. M. Byrne, Ph.D. thesis, Cornell University (Ithaca, NY), 2006.
    • Carbonylation of 2h using 5 mol% 1/BnOH for 6 h yielded 37% oxazinone 3h. Longer reaction time (24 h) and higher catalyst loading (10 mol%) left no signs of either oxazoline 2h or oxazinone 3h, but gave exclusively 2-(4-tert-butylphenyl)-4-ethyl-2-oxazalone. For details, see C. M. Byrne, Ph.D. thesis, Cornell University (Ithaca, NY), 2006.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.