Regioselective and enantioselective synthesis of seven-membered ring cyclic arylguanidine and urea derivatives

Tetrahedron

Volumn 60, Issue 1, 2004, Pages 73-79

  Zhou, Hai Bing ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Arylguanidine; Cyclization; Palladium; Seven membered ring; Urea

Indexed keywords

1 BUTYL 3 (3 CHLOROPHENYL) 4 VINYL 2H 1,3 DIAZEPIN 2 YLIDENE (3 CHLOROPHENYL)AMINE; 1 BUTYL 4 METHYL 2 VINYLPYRROLIDINE; 1 BUTYL 6 METHYL 3 (3 CHLOROPHENYL) 4 VINYL 2H 1,3 DIAZEPIN 2 YLIDENE (3 CHLOROPHENYL)AMINE; 1 CYCLOHEXYL 3 (3 CHLOROPHENYL) 4 VINYL 2H 1,3 DIAZEPIN 2 YLIDENE (3 CHLOROPHENYL)AMINE; BIS(2 CHLOROPHENYL)CARBODIIMIDE; CYANAMIDE; GUANIDINE DERIVATIVE; PALLADIUM ACETATE; PENTANE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; ARYLATION; CIS ISOMER; CYCLIZATION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

EID: 0346335807     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.088     Document Type: Article

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44. Other chiral ligands, i.e. (R)-BINAP type ligands, proved less effective in the reaction of 1a with 5b , and only gave 15% ee, in low product yield and conversion. When (R)-DIOP was used, the product was isolated in good yield and conversion, but no enantiodiscrimination was found. However, no reaction occurred when chiral ligands DuPHOS was used as chiral ligands. Use of 1b as the substrate, and other (R)-Tol-BINAP, (R)-BINAP or (-)-Me-DuPHOS as chiral ligands, gave no reaction with 5b . Chiral ligands such as (R,R)-DIOP, (S,S)-BDPP and (R,R)-BPPM can give the product in 12-33% yields but in 0% ee.
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