Catalytic enantioselective cross-dehydrogenative coupling of 3, 6-dihydro-2H-pyrans with aldehydes. Issue 9 (20th March 2019)

• Record Type: Journal Article
• Authors: Xin, Xiaodong; Pan, Xinhui; Meng, Zhilin; Liu, Xigong; Liu, Lei
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 9(2019)
• Page Start: 1448
• Page End: 1452
• Publication Date: 2019-03-20
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo00123a
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The first catalytic asymmetric cross-dehydrogenative coupling of 3, 6-dihydro-2 H -pyrans and aldehydes with excellent enantioselectivity is described. Abstract : The existing catalytic asymmetric synthesis of enantiopure α-substituted 3, 6-dihydro-2 H -pyrans and tetrahydropyrans predominantly relies on the oxygen heterocycle construction strategy involving enantioselective cyclization of pre-functionalized olefin substrates. Given the easy availability of the cyclic ether skeleton, we disclosed the first catalytic asymmetric cross-dehydrogenative coupling of 3, 6-dihydro-2 H -pyrans and aldehydes. The reaction exhibits excellent enantioselectivity, good functional group tolerance, and wide compatibility of diverse 3, 6-dihydro-2 H -pyran and aldehyde components, thus providing a practical and economical method for enantiopure α-substituted 3, 6-dihydro-2 H -pyran synthesis.