C- and N-Selective Grignard Addition Reactions of α-Aldimino Esters in the Presence or Absence of Zinc(II) Chloride: Synthetic Applications to Optically Active Azacycles.
Highly practical synthetic methods were developed for the C- and N-selective Grignard addition reactions of N-4-MeOC6H4-protected α-aldimino esters in the presence or absence of zinc(II) chloride. Diastereoselective C-alkyl addition, tandem C-alkyl addition-N-alkylation, and some transformations to synthetically useful optically active azacycles were demonstrated.
†Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
Manabu
M
Hatano
†Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
Kenji
K
Yamashita
†Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.|‡Japan Science and Technology Agency (JST), CREST, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
Kazuaki
K
Ishihara
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D009904:Optical Rotation; D009942:Organometallic Compounds / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
D001372:Aza Compounds; D002712:Chlorides; D004952:Esters; D009942:Organometallic Compounds; D017967:Zinc Compounds; C016837:zinc chloride