Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions

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• 作者：Kumar Dilip Ashtekar ; Xinliang Ding ; Edmond Toma ; Wei Sheng ; Hadi Gholami ; Christopher Rahn ; Paul Reed ; Babak Borhan
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 19, 2016
• 年：2016
• 卷：18
• 期：16
• 页码：3976-3979
• 全文大小：381K
• 年卷期：0
• ISSN：1523-7052

文摘

Utilizing two robust C–C bond-forming reactions, the Baylis–Hillman reaction and the Diels–Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a “one-pot” sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.