Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C

Takayuki Kudoh, Yuya Araki, Natsumi Miyoshi, Mizuho Tanioka, and Akira Sakakura* 
Asian J. Org. Chem.2017, 6 (12), 1760–1763.   (Published online: Oct 19, 2017) 
DOI: 10.1002/ajoc.201700568 

β,β-Disubstituted β-amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials.  In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocenter with different configuration.  Based on this methodology, a total synthesis of manzacidins A and C has been achieved.