共 44 条
Stereoelectronic versus Steric Tuning in the Prins Cyclization Reaction: Synthesis of 2,6-trans Pyranyl Motifs
被引:43
作者:

Hu, Xu-Hong
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

Liu, Feng
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

Loh, Teck-Peng
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
机构:
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
关键词:
DIELS-ALDER REACTION;
STEREOSELECTIVE-SYNTHESIS;
NATURAL-PRODUCTS;
CHIRAL CROTYLSILANES;
ALDEHYDES;
TETRAHYDROPYRANS;
DIHYDROPYRANS;
ALCOHOLS;
CONSTRUCTION;
SUBSTITUENTS;
D O I:
10.1021/ol900196w
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The use of carboalkoxyl allenic alcohol for the efficient synthesis of pyranyl motifs via Prins cyclization is described. This method provides easy access to 2,6-trans dihydropyrans in good yield and high diastereoselectivity.
引用
收藏
页码:1741 / 1743
页数:3
相关论文
共 44 条
- [1] Stereochemistry of nucleophilic substitution reactions depending upon substituent: Evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) : 15521 - 15528Ayala, L论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USALucero, CG论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USARomero, JAC论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USATabacco, SA论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USAWoerpel, KA论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
- [2] Tandem glycolate Claisen rearrangement/ring-closing metathesis: A stereochemically general synthesis of substituted dihydropyran-2-carboxylates[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) : 3160 - 3161Burke, SD论文数: 0 引用数: 0 h-index: 0机构: Univ Wisconsin, Dept Chem, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, Madison, WI 53706 USANg, RA论文数: 0 引用数: 0 h-index: 0机构: Univ Wisconsin, Dept Chem, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, Madison, WI 53706 USAMorrison, JA论文数: 0 引用数: 0 h-index: 0机构: Univ Wisconsin, Dept Chem, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, Madison, WI 53706 USAAlberti, MJ论文数: 0 引用数: 0 h-index: 0机构: Univ Wisconsin, Dept Chem, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
- [3] Structural evidence that alkoxy substituents adopt electronically preferred pseudoaxial orientations in six-membered ring dioxocarbenium ions[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (15) : 5322 - 5323Chamberland, S论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USAZiller, JW论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USAWoerpel, KA论文数: 0 引用数: 0 h-index: 0机构: Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
- [4] Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings[J]. TETRAHEDRON LETTERS, 2007, 48 (01) : 37 - 41Chan, Kok-Ping论文数: 0 引用数: 0 h-index: 0机构: Nanyang Technol Univ, Div Chem & Chem Biol, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Chem Biol, Singapore 637616, SingaporeSeow, Ai-Hua论文数: 0 引用数: 0 h-index: 0机构: Nanyang Technol Univ, Div Chem & Chem Biol, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Chem Biol, Singapore 637616, SingaporeLoh, Teck-Peng论文数: 0 引用数: 0 h-index: 0机构: Nanyang Technol Univ, Div Chem & Chem Biol, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Chem Biol, Singapore 637616, Singapore
- [5] Prins cyclizations in silyl additives with suppression of epimerization: Versatile tool in the synthesis of the tetrahydropyran backbone of natural products[J]. ORGANIC LETTERS, 2005, 7 (20) : 4491 - 4494Chan, KP论文数: 0 引用数: 0 h-index: 0机构: Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, SingaporeLoh, TP论文数: 0 引用数: 0 h-index: 0机构: Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore
- [6] Lewis acid-catalyzed one-pot crossed Prins cyclizations using allylchlorosilane as allylating agent[J]. TETRAHEDRON LETTERS, 2004, 45 (45) : 8387 - 8390Chan, KP论文数: 0 引用数: 0 h-index: 0机构: Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, SingaporeLoh, TP论文数: 0 引用数: 0 h-index: 0机构: Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
- [7] 5-Exocyclic products, 2,3,5-trisubstituted tetrahydrofurans via prins-type cyclization[J]. ORGANIC LETTERS, 2006, 8 (16) : 3617 - 3619Chavre, Satish N.论文数: 0 引用数: 0 h-index: 0机构: Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South KoreaChoo, Hyunah论文数: 0 引用数: 0 h-index: 0机构: Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South KoreaCha, Joo Hwan论文数: 0 引用数: 0 h-index: 0机构: Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South KoreaPae, Ae Nim论文数: 0 引用数: 0 h-index: 0机构: Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South KoreaChoi, Kyung Il论文数: 0 引用数: 0 h-index: 0机构: Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South KoreaCho, Yong Seo论文数: 0 引用数: 0 h-index: 0机构: Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea Korea Inst Sci & Technol, Biochem Res Ctr, Seoul 130650, South Korea
- [8] Revisiting the Maitland-Japp reaction. Concise construction of highly functionalised tetrahydropyran-4-ones[J]. CHEMICAL COMMUNICATIONS, 2005, (08) : 1061 - 1063Clarke, PA论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandMartin, WHC论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandHargreaves, JM论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandWilson, C论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, EnglandBlake, AJ论文数: 0 引用数: 0 h-index: 0机构: Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
- [9] Oxonia-cope rearrangement and side-chain exchange in the prins cyclization[J]. ORGANIC LETTERS, 2002, 4 (04) : 577 - 580Crosby, SR论文数: 0 引用数: 0 h-index: 0机构: Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, EnglandHarding, JR论文数: 0 引用数: 0 h-index: 0机构: Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, EnglandKing, CD论文数: 0 引用数: 0 h-index: 0机构: Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, EnglandParker, GD论文数: 0 引用数: 0 h-index: 0机构: Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, EnglandWillis, CL论文数: 0 引用数: 0 h-index: 0机构: Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
- [10] Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of δ-trialkylsilyloxy substituted ketones:: Total synthesis of (-)-centrolobine[J]. ORGANIC LETTERS, 2003, 5 (21) : 3883 - 3885Evans, PA论文数: 0 引用数: 0 h-index: 0机构: Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USACui, J论文数: 0 引用数: 0 h-index: 0机构: Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USAGharpure, SJ论文数: 0 引用数: 0 h-index: 0机构: Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA