Catalytic Enantioselective Synthesis of the Second Generation Histamine Antagonist Cetirizine Hydrochloride
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- 作者：Corey ; E. J. ; Helal ; Christopher J.
- 刊名：Tetrahedron Letters
- 出版年：1996
- 出版时间：July 8, 1996
- 年：1996
- 卷：37
- 期：28
- 页码：4837-4840
- 全文大小：205 K
文摘
The first enantioselective synthesis of cetirizine hydrochloride (1) has been developed using the highly stereospecific chiral oxazaborolidine (CBS) reduction of 4-[η6-chromium tricarbonylbenzoyl]chlorobenzene to establish the benzhydryl stereocenter. The chromium tricarbonyl unit also served as stereocontroller to allow the stereospecific displacement of hydroxyl by amino at the benzylic stereocenter, as outlined in Scheme 1.