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Stereoselective amination of chiral benzylic ethers using chlorosulfonyl isocyanate: total synthesis of (+)-sertraline.

The Journal of organic chemistry (2011-10-26)
Sang Hwi Lee, In Su Kim, Qing Ri Li, Guang Ri Dong, Lak Shin Jeong, Young Hoon Jung
RESUMEN

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.

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Sigma-Aldrich
1-Naphthol, ReagentPlus®, ≥99%
Sigma-Aldrich
1-Naphthol, puriss. p.a., reag. Ph. Eur., ≥99% (GC)
Sigma-Aldrich
1-Naphthol, BioXtra, ≥99%