Highly enantioselective aldol reaction of acetaldehyde and isatins only with 4-hydroxydiarylprolinol as catalyst: concise stereoselective synthesis of (R)-convolutamydines B and E, (-)-donaxaridine and (R)-chimonamidine

Tetrahedron

Volumn 66, Issue 7, 2010, Pages 1441-1446

  Chen, Wen Bing ^a,b   Du, Xi Lin ^c   Cun, Lin Feng ^a   Zhang, Xiao Mei ^a   Yuan, Wei Cheng ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c FOURTH MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Acetaldehyde; Aldol reaction; Asymmetric catalysis; Isatins; Organocatalysis

Indexed keywords

1 ALLYL 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 1 BENZYL 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 3 HYDROXY 3 (2 HYDROXYETHYL) 1 METHYLINDOLIN 2 ONE; 3 HYDROXY 3 (2 HYDROXYETHYL) 5 METHOXYINDOLIN 2 ONE; 3 HYDROXY 3 (2 HYDROXYETHYL) 5 METHYLINDOLIN 2 ONE; 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 4 BROMO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 4 CHLORO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 4,6 DIBROMO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 5 BROMO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 5 CHLORO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 5,7 DIBROMO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 6 BROMO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; 6 CHLORO 3 HYDROXY 3 (2 HYDROXYETHYL)INDOLIN 2 ONE; ACETALDEHYDE; ALKALOID DERIVATIVE; CHIMONAMIDINE; CONVOLUTAMYDINE B; CONVOLUTAMYDINE E; DONAXARIDINE; ISATIN DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 74049114934     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.041     Document Type: Article

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68. 2H as necessary additive under 4 °C.
69. The optically active (R)-convolutamydine E was obtained with 250 mg (white solid).
70. About the detailed procedure, see Experimental section.
71. The absolute configuration of chimonamidine (9) was R assigned by comparison of the sign of the optical rotation with reported data in Ref. 2b.