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Volumn 350, Issue 7-8, 2008, Pages 1023-1045

Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines

Author keywords

Aldimines; Bisoxazolines; Catalysis; Enantioselective addition; Organolithium reagents

Indexed keywords


EID: 53849089248     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800017     Document Type: Article
Times cited : (32)

References (153)
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    • For diastereoselective radical additions, see: j) G. K. Friestad, Tetrahedron 2001, 57, 5461.
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    • For an excellent, current compilation of reviews and papers on the catalytic, enantioselective addition of organometallic reagents to imines see
    • For an excellent, current compilation of reviews and papers on the catalytic, enantioselective addition of organometallic reagents to imines see: E. Skucas, M.-Y. Ngai, V. Komanduri, M. J. Krische, Acc. Chem. Res. 2007, 40, 1394.
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    • The asymmetric Strecker reaction has also been extensively developed in recent years. For recent reviews see: a
    • The asymmetric Strecker reaction has also been extensively developed in recent years. For recent reviews see: a) H. Gröger, Chem. Rev. 2003, 103, 2795;
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    • Chemical Abstracts Registry No. 90-39-1. Index name: (7S,7a R,14S,14aS)-dodecahydro-7,14-methano-2H, 6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocine.
    • Chemical Abstracts Registry No. 90-39-1. Index name: (7S,7a R,14S,14aS)-dodecahydro-7,14-methano-2H, 6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocine.
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    • Unfortunately, under the same conditions, Grignard reagents (MeMgBr, MeMgI) did not react with imine 11. Phenylmagnesium bromide gradually reacted at -10°C in ther and toluene, but 20 was produced in low conversion (21-37%) and poor selectivity (ca. 56.0:44.0 er). [46] TMSCl, TBSCl, and TIPSCl (1.0 equiv.) were tested.
    • Unfortunately, under the same conditions, Grignard reagents (MeMgBr, MeMgI) did not react with imine 11. Phenylmagnesium bromide gradually reacted at -10°C in ther and toluene, but 20 was produced in low conversion (21-37%) and poor selectivity (ca. 56.0:44.0 er). [46] TMSCl, TBSCl, and TIPSCl (1.0 equiv.) were tested.
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    • Oxidative cleavage of p-methoxyphenyl group of 17 failed. The absolute configuration of 17 was determined by hydrogenation to 16 (Pd/C, EtOAc, 79%) and comparison of optical rotations.
    • Oxidative cleavage of p-methoxyphenyl group of 17 failed. The absolute configuration of 17 was determined by hydrogenation to 16 (Pd/C, EtOAc, 79%) and comparison of optical rotations.
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    • Coordination of the imine to complex 12ac·MeLi can be achieved with MNDO if the optimization procedure is stopped at a gradient norm of 3
    • Coordination of the imine to complex 12ac·MeLi can be achieved with MNDO if the optimization procedure is stopped at a gradient norm of 3. However, this geometry exhibits one imaginary frequency.
    • However, this geometry exhibits one imaginary frequency


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.