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Volumn 7, Issue 2, 2005, Pages 355-358

Unprecedented catalytic asymmetric reduction of N-H imines

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; IMINE; LITHIUM BIS(TRIMETHYLSILYL)AMIDE; METHANOL; UNCLASSIFIED DRUG;

EID: 13444302540     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047431x     Document Type: Article
Times cited : (104)

References (36)
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    • Diastereoselective addition of aryl groups to chiral oxazolidines: (c) Ishii, A.; Miyamoto, F.; Higashiyama, K.; Mikami, K. Chem. Lett. 1998, 119-120. (d) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382.
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    • note
    • 3OD) δ -72.0.
  • 31
  • 32
    • 85039475575 scopus 로고    scopus 로고
    • note
    • 3Br [M + H] 253.9792, found 253.9790.
  • 33
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    • note
    • D = +11.2 (c = 1.5, MeOH).
  • 34
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    • note
    • For example enantioselective reduction of N-H imine 7 with 5 mol % of commercially available (R)-methyl-OAB afforded amine (S)-14c in 90-91% ee on a 10 g scale. See Supporting Information.
  • 36
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    • note
    • In a single unoptimized experiment we observed that isolated methanol adduct 7c containing less than 5% N-H imine underwent enantioselective reduction with (S)-methyl-OAB and catecholborane in toluene at -15°C to afford amine 14c in 72% yield and 78% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.