Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
Org Lett. 2016 Aug 19;18(16):3976-9. doi: 10.1021/acs.orglett.6b01742. Epub 2016 Aug 3.
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.
利用两个强大的 C-C 键形成反应，即 Baylis-Hillman 反应和 Diels-Alder 反应，我们报告了一种通过两步[4+2]环加成反应高度对映选择性、区域选择性和非对映选择性合成六氢-2H-色烯的方法。这些串联和形式的环加成反应也可以作为“一锅法”序列进行，以获得相应的杂环，在极好的收率和立体选择性下构成多达五个连续的立体中心。
