Chiral Preparation of C2-Symmetric 4-Cyclopentene-1,3-diol

Kimura, Seiko; Ehama, Ryoko; Inomata, Kohei

doi:10.1055/s-2002-31949

Cited by 6 publications

(2 citation statements)

References 6 publications

(8 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction mixture was stirred under air for 5 min and concentrated. The crude product was purified by silica gel chromatography (100% EtOAc) to afford the product as colorless oil (266 mg, 68%): R f = 0.20 (100% EtOAc); IR (neat) 3420 cm –1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 6.05–6.01 (m, 2H), 5.07 (t, J = 4.8 Hz, 2H), 2.10 (t, J = 5.0 Hz, 2H), 1.56 (br s, 2H); 13 C NMR (101 MHz, CDCl 3 ) δ 137.4, 76.4, 44.4; m / z (ESI+) found [M + H] + 100.0518, C 5 H 8 O 2 requires 100.0524; [α] D 23.6 +232 ( c 1.0, MeOH) [lit [α] D 27 +228.1 ( c 1.04, MeOH)].…”

Section: Experimental Sectionmentioning

confidence: 99%

“…38 Various RCM conditions were tried, with the best results being obtained using Grubbs II 40 catalyst, which provided the cyclized product in 68% yield. In this way, diol 5 could be obtained in multigram amounts (enantiopure 5 is also available via enzymatic resolution 41 ). We were somewhat surprised to find that it was difficult to selectively carry out the monoprotection of 5 to afford ethers like 6 .…”

mentioning

confidence: 99%

See 1 more Smart Citation

Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

2013

View full text Add to dashboard Cite

show abstract

Section: Experimental Sectionmentioning

confidence: 99%

mentioning

confidence: 99%

Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

2013

View full text Add to dashboard Cite

show abstract

Retro‐Diels–Alder Protocol for the Synthesis of Pyrrolo[1,2‐a]pyrimidine and Pyrimido[2,1‐a]isoindole Enantiomers

et al. 2013

View full text Add to dashboard Cite

A simple protocol was introduced to prepare several enantiomerically pure heterocycles by using (–)‐(1R,2R,3S,4S)‐3‐aminonorbornene‐2‐carboxylic acid as a chiral auxiliary. The protocol is based on a domino ring‐closure reaction, in which the relative configuration of the new asymmetric center is controlled by the stereochemistry of the amino acid, followed by a microwave‐induced retro‐Diels–Alder reaction.

show abstract

Synthesis of 1,3‐cis‐Fused Tricyclic System through Regio‐ and Stereoselective Epoxidation and Ring‐Rearrangement Metathesis: Access To Basic Core of Presilphiperfolanols

2023

View full text Add to dashboard Cite

Here, we report a new synthetic approach to a highly strained 1,3-fused cis-cis-cis-5/5/6 tricyclic system that appeared among the presilphiperfolanol analogues. The cis-fusion of six-membered ring to a diquinane moiety is accomplished by substratecontrolled regio-and stereoselective epoxidation, and ringrearrangement metathesis (RRM) sequence. In this regard, both early-, and late-stage epoxidation and RRM reactions were studied. The target compound, cis-cis-cis-5/5/6 tricyclic ketone with an α,β-oxirane ring can serve as a key building block to produce various presilphiperfolanol analogues. The cis-cis-cis-5/ 5/6-tricyclic-α,β-epoxyketone can also act as masked enone and therefore useful for various chemical transformations in organic synthesis. The short synthetic sequence disclosed here may be useful to design various biologically important molecules. The newly reported molecules are well-characterized by NMR, HRMS, and IR spectral data.

show abstract

Chiral Preparation of C2-Symmetric 4-Cyclopentene-1,3-diol

Abstract: Optically pure C 2

Cited by 6 publications

References 6 publications

Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

Retro‐Diels–Alder Protocol for the Synthesis of Pyrrolo[1,2‐a]pyrimidine and Pyrimido[2,1‐a]isoindole Enantiomers

Synthesis of 1,3‐cis‐Fused Tricyclic System through Regio‐ and Stereoselective Epoxidation and Ring‐Rearrangement Metathesis: Access To Basic Core of Presilphiperfolanols

Contact Info

Product

Resources

About