Enantioselective asymmetric Pictet-Spengler reaction catalyzed by diisopinocampheylchloroborane

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1249-1252

  Kawate, Tomohiko ^a   Yamada, Hideki ^a   Soe, Than ^a   Nakagawa, Masako ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CARBOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030005588     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00134-6     Document Type: Article

References (26)

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20. 3 solution.
21. 3 solution and the mixture was warmed up to room temperature. Usual workup and purification with silica gel column chromatography gave 2a (101 mg, 92%). The optically purity of 2a was measured with hplc using a chiral column, DAICEL chiralcel-OD(hexane:isopropanol=90:10, 1 ml/min, 254 nm) and was 75%ee. Retention time of the major enantiomer was 13.48 min and that of the minor isomer was 25.14 min.
22. 13
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24. 16 T. Kawate, H. Tei, Y. Yonezawa, T. Hino, and M. Nakagawa, unpublished data.
25. Calculated enantiomeric excess of 3a and 3e suggests partial racemization accompanied by the reduction steps. Reduction procedure with complete retension is under investigation.
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