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

• DOI: 10.1021/acs.orglett.6b01742
• Publication Date: 2016-08-03T12:47:37Z
• Authors: Kumar Dilip Ashtekar; Xinliang Ding; Edmond Toma; Wei Sheng; Hadi Gholami; Christopher Rahn; Paul Reed; Babak Borhan
• Keywords: Cycloaddition Reaction; Molecular Structure; Benzopyrans; 01 natural sciences; 0104 chemical sciences

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