Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol–Prins Strategy

SJ Álvarez-Méndez, M Fariña-Ramos… - The Journal of …, 2018 - ACS Publications
A direct and general method for the synthesis of naturally occurring 2, 3, 4, 5, 6-
pentasubstituted tetrahydropyrans has been developed, employing β, γ-unsaturated N-acyl …

The Evans Aldol–Prins cyclization: a general and stereoselective method for the synthesis of 2, 3, 4, 5, 6-pentasubstituted tetrahydropyrans

SJ Álvarez-Méndez, C García, VS Martín - Chemical communications, 2016 - pubs.rsc.org
A general and stereoselective method to synthesize 2, 3, 4, 5, 6-pentasubstituted
tetrahydropyrans in three steps starting from three different aldehydes is described. Key …

Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ Prins-type cyclization reaction

J Yang, GS Viswanathan, CJ Li - Tetrahedron letters, 1999 - Elsevier
The reaction of aldehyde with homoallyl alcohols mediated by indium trichloride generated
4-chlorotetrahydropyrans in high yields and with high stereoselectivity. The same type of …

[HTML][HTML] Efficient, highly diastereoselective MS 4 Å-promoted one-pot, three-component synthesis of 2, 6-disubstituted-4-tosyloxytetrahydropyrans via Prins cyclization

N Ahmed, NK Konduru - Beilstein Journal of Organic …, 2012 - beilstein-journals.org
A simple, efficient and highly diastereoselective one-pot three-component synthesis of
functionalized 2, 6-disubstituted-4-tosyloxytetrahydropyrans was performed. The synthesis …

Silyl enol ether prins cyclization: Diastereoselective formation of substituted tetrahydropyran-4-ones

GC Tay, CY Huang, SD Rychnovsky - The Journal of organic …, 2014 - ACS Publications
A diastereoselective synthesis of cis-2, 6-disubstituted tetrahydropyran-4-ones was
developed. The key step of this methodology, a silyl enol ether Prins cyclization, was …

Spiro‐and Bicycloannulation of Sulfoximine‐Substituted 2‐Hydroxy‐dihydropyrans: Enantioselective Synthesis of Spiroketals, Spiroethers, and Oxabicycles and …

M Lejkowski, P Banerjee, G Raabe… - European Journal of …, 2014 - Wiley Online Library
A modular enantioselective synthesis of spiroketals, spiroethers, and oxabicycles, each
containing a dihydropyran subunit, is described. It is based on the 2, 2‐spiro‐and 2, 6 …

Stereoselective synthesis of 4-O-tosyltetrahydropyrans via Prins cyclization reaction of enol ethers

S Sarkar, N Devi, B Porashar, S Ruidas, AK Saikia - SynOpen, 2019 - thieme-connect.com
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Cerium (IV) sulfate catalyzed one-pot three-component diastereo selective synthesis of 4-amidotetrahydropyrans

NP Selvam, PT Perumal - Canadian Journal of Chemistry, 2009 - cdnsciencepub.com
A convenient and diastereoselective one-pot synthesis of cis-4-amidotetrahydropyrans is
described. This simple protocol involves Prins cyclization of homoallylic alcohol and …

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

YS Kim, JK Lee, AN Pae, YS Cho, SJ Min - Synlett, 2013 - thieme-connect.com
We have described a highly diastereoselective synthesis of 2, 6-disubstituted 4-
(dimethoxymethyl) tetrahydropyrans via TMSOTf-promoted Prins–pinacol reaction of …

Three-component, one-pot diastereoselective synthesis of 4-amidotetrahydropyrans via the Prins–Ritter reaction sequence

JS Yadav, BVS Reddy, S Aravind, GN Kumar… - Tetrahedron, 2008 - Elsevier
Three-component coupling of carbonyl compounds, homoallylic alcohols, and nitriles has
been achieved using 20mol% of phosphomolybdic acid (PMA) at ambient temperature via …