Treatment of N,N-dibenzylamino alcohols with sulfonyl chloride leads to rearranged β-chloro amines, precursors to β-amino acids, and not to tetrahydroisoquinolines

Organic Letters

Volumn 2, Issue 5, 2000, Pages 647-649

  Weber, Klaus ^a   Kuklinski, Stephan ^a   Gmeiner, Peter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID; AMINOALCOHOL; ISOQUINOLINE DERIVATIVE; SULFINIC ACID DERIVATIVE; SULFONYL CHLORIDE;

ARTICLE; CHEMISTRY;

AMINES; AMINO ACIDS; AMINO ALCOHOLS; ISOQUINOLINES; SULFINIC ACIDS;

EID: 0034624592     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991402i     Document Type: Article

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15. +).
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17. +).
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21. For previous homologations of amino acids, see: Podlech, J.; Seebach, D. Liebigs Ann. Chem. 1995, 1217. Caputo, R.; Cassano, E.; Longobardo, L. Palumbo, G. Tetrahedron 1995, 51, 12337 and references therein.
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24. 30ClNO: C, 79.02; H, 6.63; N, 3.07. Found: C, 78.51; H, 6.47; N, 3.74.
25. 2Ph), 7.00-7.10 (m, 2H, ar), 7.18-7.40 (m, 13H, ar).
26. 2O: C, 83.37; H, 6.77; N, 6.27. Found: C, 83.05; H, 6.85; N, 6.46.
27. 3) for the (3S,2′R)-configured urea. The synthetic material proved isomerically pure.