基于反应机理的烯丙基硼化和受生物启发的氧杂-Michael 环化促进的功能化四氢吡喃的立体发散合成。
Stereodivergent Synthesis of Functionalized Tetrahydropyrans Accelerated by Mechanism-Based Allylboration and Bioinspired Oxa-Michael Cyclization.
机构信息
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry (CAS), 345 Lingling Road, Shanghai, 200032, China.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, China.
出版信息
Angew Chem Int Ed Engl. 2016 May 17;55(21):6280-4. doi: 10.1002/anie.201600558. Epub 2016 Apr 13.
A stereodivergent strategy enabled by bioinspired oxa-Michael cyclization was developed for the synthesis of functionalized tetrahydropyrans on the basis of the inherent symmetry in 1,3-diols, the symmetries of which were tunable by stereoselective hydroboration of an allene with a variety of alkylborane reagents and subsequent allylation of an aldehyde. The mechanism-based utilization of monoalkyl borane in the hydroboration and allylation cascade is unprecedented.
受生物启发的氧杂-Michael 环化的立体发散策略被开发用于基于 1,3-二醇固有对称性的功能化四氢吡喃的合成，二醇的对称性可以通过各种烷基硼烷试剂对丙二烯的立体选择性硼氢化作用以及随后的醛的烯丙基化作用来调节。在硼氢化和烯丙基化级联反应中，单烷基硼烷的基于机制的利用是前所未有的。
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