Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: total synthesis of (+)-sertraline.
The stereoselective amination of various chiral benzylic ethers using chlorosulfonyl isocyanate is developed, and the application of this method to the total synthesis of a potent antidepressant, (+)-sertraline, from readily available 1-naphthol is also described.
School of Pharmacy, Sungkyunkwan University, Suwon 440-746, Republic of Korea.
Sang Hwi
SH
Lee
In Su
IS
Kim
Qing Ri
QR
Li
Guang Ri
GR
Dong
Lak Shin
LS
Jeong
Young Hoon
YH
Jung
D000586:Amination; D000928:Antidepressive Agents / Q000138:chemical synthesis*; D001554:Benzene / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D006801:Humans; D017953:Isocyanates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D020280:Sertraline / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000928:Antidepressive Agents; D004987:Ethers; D017953:Isocyanates; D009284:Naphthols; C487390:chlorosulfonyl isocyanate; C029350:1-naphthol; D001554:Benzene; D020280:Sertraline