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Volumn 42, Issue 47, 2003, Pages 5868-5870

Practical Asymmetric Synthesis of Vicinal Diamines through the Catalytic Highly Enantioselective Alkylation of Glycine Amide Derivatives

Author keywords

Alkyl halides; Alkylation; Asymmetric catalysis; Phase transfer catalysis; Vicinal diamines

Indexed keywords

CATALYSIS; DERIVATIVES; SYNTHESIS (CHEMICAL);

EID: 0346158950     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352658     Document Type: Article
Times cited : (40)

References (45)
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    • note
    • Cyclopentyl methyl ether, kindly supplied by Zeon Corporation, Japan, has a higher boiling point (106 °C) than tert-butyl methyl ether. Both ethers are regarded as a potential substitute for diethyl ether.
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    • note
    • No loss of enantiomeric excess was observed, as determined by HPLC analysis.
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    • The catalytic enantioselective preparation of α-amino acid derivatives that contain a tertiary β carbon atom from glycine anion equivalents is commonly regarded as extremely difficult. For a diastereoselective approach, see: a) J. M. McIntosh, R. K. Leavitt, P. Mishra, K. C. Cassidy, J. E. Drake, R. Chadha, J. Org. Chem. 1988, 53, 1947;
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    • 11a] an extra reaction step is sometimes necessary, for example, alkylation with a reactive secondary allylic halide and subsequent reduction; see: e) J. M. McIntosh, R. K. Leavitt, Tetrahedron Lett. 1986, 27, 3839.
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    • note
    • 2 as the solvent at -78°C to -40°C did not lead to the formation of the product, and 2b (R=iPr) was obtained in approximately 23 % yield, although with only 7 % ee, after 5 h at -20°C.
  • 40
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    • note
    • The absolute configuration of the product 8 was determined to be R by X-ray crystallographic analysis after conversion into a dipeptide with N-benzyloxycarbonyl-L-alanine; see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.