57323-08-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 1787, 1982 DOI: 10.1021/jo00348a045

InChI:InChI=1/C9H14O3/c10-6-2-4-8-12-9-5-1-3-7-11-9/h2,4,6,9H,1,3,5,7-8H2/b4-2+

Upstream product

• 57323-06-5 (2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol 
• 58201-77-7 4-(tetrahydro-2H-pyran-2-yl)oxy-2-butenol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 77741-47-0 (E)-4-((tetrahydro-2H-pyran-2-yl)oxy)but-2-en-1-ol 
• 41793-29-7 (Z)-4-chloro-1-<(tetrahydropyran-2-yl)oxy>but-2-ene 

Downstream Products

• 104951-06-6 Ethyl 2-oxo-5-phenylsulfinyl-6-tetrahydropyranyloxy-3a,4,5,6-tetrahydro(3H)benzofuran-5-carboxylate 
• 105897-82-3 (5S,6R)-6-((E)-3-Methyl-but-1-enyl)-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enone 
• 105897-83-4 (1S,5S,6R)-6-((E)-3-Methyl-but-1-enyl)-5-(tetrahydro-pyran-2-yloxymethyl)-1-vinyl-cyclohex-2-enol 
• 105897-81-2 Trimethyl-[(1S,5S,6R)-6-((E)-3-methyl-but-1-enyl)-5-(tetrahydro-pyran-2-yloxymethyl)-cyclohex-2-enyloxy]-silane 
• 1264720-67-3 C₁₇H₂₄O₃ 
• 104951-06-6 (5S,6R)-5-Benzenesulfinyl-2-oxo-6-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,4,5,6-hexahydro-benzofuran-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl2C(CN)2

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The catalytic oxidation of the allylic alcohols 1d-n with iodosobenzene diacetate, mediated by the [CrIII(salen)]X complex, affords the respective enones in excellent chemoselectivity for Cl- as counterion [complex A(Cl)], while for the counterions TfO- [complex A(TfO)] and PF6- [complex A(PF6)] nearly equal amounts of enone and epoxide are observed. This counterion-dependent oxidation of allylic alcohols by CrIII(salen) complexes is rationalized in terms of Lewis acid catalysis by the complex A(Cl) and redox catalysis for A(TfO) and A(PF6).

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Transannular Diels-Alder reactions of 14-membered macrocyclic trienes possessing a methyl substituent on both the diene and dienophile moiety have been investigated. Macrocyclic structures la, lb, and lc having cis-trans-trans (CTT), trans-cis-trans (TCT), and trans-trans-trans (TTT) geometries could be stereoselectively constructed by coupling appropriately functionalized dienes 5 and dienophile 4 following an intramolecular displacement of an allylic halide by the anion of an appropriately located dimethyl malonate unit. The transannular Diels-Alder reaction performed on la led to a mixture of four major tricyclic products, including 34 possessing the unexpected trans-anti-cis (TAC) stereochemistry. When heated at 300°C, macrocycle lb underwent an unique conversion via an ene-retroene, Diels-Alder process, producing the unexpected tricycle 41 (racemic form) containing five contiguous chiral centers. A rationale for the above experimental facts is presented. In contrast to the previous results, the transannular Diels-Alder reaction of macrocycle lc was straightforward, producing a 95% isolated yield of trans-anti-cis (TAC) tricycle 34. This investigation demonstrates a general methodology for the stereocontrolled synthesis of 1, 2-dimethyl A.B.C[6.6.6] tricyclic compounds, which are potential precursors to polycyclic natural products such as steroids and terpenes.

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