Enantioselective Preparation of Alcohols and Amines: The Lam Synthesis of (+)-Tanikolide

Abstract

Takashi Ooi of Nagoya University effected (J. Am. Chem. Soc. 2010, 132, 12240) the enantioselective protonation of ketene silyl acetals such as 1 to give 2 in high ee. Hyeon-Kyu Lee of the Korean Research Institute of Chemical Technology achieved (Org. Lett. 2010, 12, 4184) high ee in the hydrogenation of the cyclic sulfamidate 3 to 4. Doo Ok Jang of Yonsei University combined (J. Am. Chem. Soc. 2010, 132, 12168) the nucleophilic allyl indium with a protonated chiral amine to effect homologation of 5 to 6. Ryo Shintani and Tamio Hayashi of Kyoto University reported (Org. Lett. 2010, 12, 4106) a related advance with tetraarylborates. Kazuaki Ishihara, also of Nagoya University (Org. Lett. 2010, 12, 3502) and Yoshihiro Sohtome and Kazuo Nagasawa of the Tokyo University of Agriculture and Technology (Angew. Chem. Int. Ed. 2010, 49, 9254) devised conditions for adding malonate to imines such as 7. Professors Shintani and Hayashi also employed (J. Am. Chem. Soc. 2010, 132, 13168) tetraarylborates to convert 9 to the α-quaternary amine 10. Professor Ooi (Angew. Chem. Int. Ed. 2010, 49, 5567) and Wanbin Zhang of Shanghai Jiao Tong University (J. Am. Chem. Soc. 2010, 132, 15939) prepared α-quaternary amino acids such as 12 by nucleophilic rearrangement of 11. Keiji Maruoka, also of Kyoto University, reported (J. Am. Chem. Soc. 2010, 132, 17074; not illustrated) a catalytic enantioselective conjugate addition approach to α-quaternary amines. Shuji Akai of the University of Shizuoka converted (Org. Lett. 2010, 12, 4900) the racemic allylic alcohol 13 to the enantiomerically enriched acetate 14 by combining V-catalyzed equilibration with lipase-catalyzed acylation. Toshiro Harada of the Kyoto Institute of Technology added (Org. Lett. 2010, 12, 5270) the alkenylboron 16 to the aldehyde 15 with high ee. Xiang Zhou of Wuhan University and Lin Pu of the University of Virginia significantly improved (Tetrahedron Lett . 2010, 51, 5024) a protocol for the enantioselective addition of aliphatic alkynes to aliphatic aldehydes. For other enantioselective additions to aldehydes (not illustrated), see J. Org. Chem. 2010, 75 , 5326 and Org. Lett. 2010, 12, 5088.