DSpace at KIST: Diastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetra-hydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization

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Diastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetra-hydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization

Authors: Kim, Young Seub; Lee, Jae Kyun; Pae, Ae Nim; Cho, Yong Seo; Min, Sun-Joon

Issue Date: 2013-10

Publisher: GEORG THIEME VERLAG KG

Citation: SYNLETT, v.24, no.17, pp.2292 - 2296

Abstract: We have described a highly diastereoselective synthesis of 2,6-disubstituted 4-(dimethoxymethyl)tetrahydropyrans via TMSOTf-promoted Prins-pinacol reaction of methylene diol with acetals. This reaction provides an efficient procedure to synthesize functionalized tetrahydropyrans containing an acetal group at the C4 position with all-cis 2,4,6 relative configuration.

Keywords: STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; STEREOCONTROLLED SYNTHESIS; TETRAHYDROPYRANS; ETHERS; SPIROKETALS; DERIVATIVES; EFFICIENT; UNITS; cyclization; Lewis acids; oxonium ion; diastereoselectivity; 2; 4; 6-trisubstituted tetrahydropyrans

ISSN: 0936-5214

URI: https://pubs.kist.re.kr/handle/201004/127601

DOI: 10.1055/s-0033-1339709

Appears in Collections:: KIST Article > 2013

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