Two Scalable Syntheses of (S)-2-Methylazetidine

详细信息    查看全文

• 作者：Matthew S. Dowling ; Dilinie P. Fernando ; Jie Hou ; Bo Liu ; Aaron C. Smith
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 1, 2016
• 年：2016
• 卷：81
• 期：7
• 页码：3031-3036
• 全文大小：485K
• ISSN：1520-6904

文摘

Two orthogonal routes for preparing (S)-2-methylazetidine as a bench stable, crystalline (R)-(−)-CSA salt are presented. One route features the in situ generation and cyclization of a 1,3-bis-triflate to form the azetidine ring, while the second route involves chemoselective reduction of N-Boc azetidine-2-carboxylic acid. Both sequences afford the desired product in good overall yields (61% and 49%) and high enantiomeric excess (>99% ee), avoid column chromatography, and are suitable for the large-scale production of this material.