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Diastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetra-hydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization
- Kim, Young Seub;
- Lee, Jae Kyun;
- Pae, Ae Nim;
- Cho, Yong Seo;
- Min, Sun-Joon
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5초록
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.
키워드
cyclization; Lewis acids; oxonium ion; diastereoselectivity; 2; 4; 6-trisubstituted tetrahydropyrans; STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; STEREOCONTROLLED SYNTHESIS; TETRAHYDROPYRANS; ETHERS; SPIROKETALS; DERIVATIVES; EFFICIENT; UNITS
- 제목
- Diastereoselective Synthesis of 2,6-Disubstituted 4-(Dimethoxymethyl)tetra-hydropyrans Using TMSOTf-Promoted Prins-Pinacol Cyclization
- 저자
- Kim, Young Seub; Lee, Jae Kyun; Pae, Ae Nim; Cho, Yong Seo; Min, Sun-Joon
- 발행일
- 2013-10
- 유형
- Article
- 저널명
- Synlett
- 권
- 24
- 호
- 17
- 페이지
- 2292 ~ 2296
- 언어
- ENG
- 출판사
- GEORG THIEME VERLAG KG
- 발행국가
- 독일
- 분량
- 5 페이지
- ISSN
- E 1437-2096
P 0936-5214