Asymmetric Intermolecular Conjugate Addition of Amino Acid Derivatives via Memory of Chirality: Total Synthesis of Manzacidin A

Asymmetric Intermolecular Conjugate Addition of Amino Acid Derivatives via Memory of Chirality: Total Synthesis of Manzacidin A

Asymmetric intermolecular conjugate addition of α-amino acid derivatives with 4 via memory of chirality has been developed. The reactions proceeded in up to 98% ee with retention of configuration at the newly formed tetrasubstituted carbon center when R = Me. The product (R = Me) was transformed int...

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Veröffentlicht in:Organic letters 2013-02, Vol.15 (4), p.864-867
Hauptverfasser: Yoshimura, Tomoyuki, Kinoshita, Tomohiko, Yoshioka, Hiroyasu, Kawabata, Takeo
Format: Artikel
Sprache:eng
Schlagworte:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Cyclization
Molecular Structure
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
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Zusammenfassung:Asymmetric intermolecular conjugate addition of α-amino acid derivatives with 4 via memory of chirality has been developed. The reactions proceeded in up to 98% ee with retention of configuration at the newly formed tetrasubstituted carbon center when R = Me. The product (R = Me) was transformed into manzacidin A.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303568f