Electroauxiliary-assisted sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen: application to the synthesis of spiro compounds.
The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.
Suga
Seiji
S
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan. suga@sbchem.kyoto-u.ac.jp
Watanabe
Mitsuru
M
Yoshida
Jun-ichi
J
D000478:Alkylation; D000588:Amines / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D004563:Electrochemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000588:Amines; D002219:Carbamates; D011759:Pyrrolidines; D013141:Spiro Compounds