Efficient construction of 1,2-dihydroquinoline and 1,2,3,4- tetrahydroquinoline rings using tandem Michael-aldol reaction

Tetrahedron Letters

Volumn 44, Issue 50, 2003, Pages 8925-8929

  Makino, Kazuishi ^a   Hara, Osamu ^b   Takiguchi, Yuko ^a   Katano, Takayuki ^a   Asakawa, Yumiko ^a   Hatano, Keiichiro ^c   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

^b MEIJO UNIVERSITY   (Japan)

^c NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

1,2,3,4 tetrahydroquinoline; 1,2 dihydroquinoline; Tandem Michael aldol reaction

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DESICCATION; DIASTEREOISOMER; DRUG EFFICACY; DRUG FORMULATION; DRUG SYNTHESIS; MICHAEL ALDOL REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0242541992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.011     Document Type: Article

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46. +), found 376.1246.
47. The chiral acceptor was prepared from the known (4S)-3-(2,2-dimethyl-[1, 3]dioxolan-4-yl)acrylic acid ethyl ester in two steps: (1) reduction of the ester with diisobutylaluminum hydride in methylene chloride in 66% yield and (2) oxidation of the allyl alcohol with activated manganese dioxide in 93% yield.
48. 3 in 77% yield.
49. 7S: C, 60.12; H, 5.48; N, 3.05. Found: C, 60.14; H, 5.41; N, 3.01.
50. 3, Z=8, Nonius Kappa CCD, Mo Kα, R=0.047, Rw=0.046. CCDC 218556 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac. uk).