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

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
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Naphthol, puriss. p.a., reag. Ph. Eur., ≥99% (GC)
Sigma-Aldrich
1-Naphthol, ReagentPlus®, ≥99%
Sigma-Aldrich
1-Naphthol, BioXtra, ≥99%
Sigma-Aldrich
1-Naphthol, SAJ special grade, ≥99.0%