Asymmetric tandem conjugate addition-allylation of chiral (p-tolylsulfinyl)pyrrolyl cinnamoyl amide

Synthesis

Volumn , Issue 10, 2003, Pages 1511-1516

  Arai, Yoshitsugu ^a   Kasai, Makoto ^a   Ueda, Kimio ^a   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Chiral sulfoxide; Conjugate addition reactions; Cuprate; Diastereoselectivity; Tandem reactions

Indexed keywords

ADDITION REACTIONS; COPPER COMPOUNDS; ESTERS; HALIDE MINERALS;

ALLYLATION;

ALKYLATION;

(4 TOLYLSULFINYL)PYRROLYLCINNAMOYL AMIDE; AMIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ALKYLATION; ALLYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CONJUGATE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0042244168     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40510     Document Type: Article

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19. 1H NMR analysis (see text). Analytical samples of 12b-15b and 12c-15c for HPLC were also prepared from optically active 4 or racemic 4 and 5 (1:1) by allylation and methallylation in 57% and 61% yields, respectively. The poor selectivities (syn/anti, ca. 1:0.9) observed are comparable to that observed for prenylation of the ester enolate.