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Volumn 4, Issue 5, 2006, Pages 877-885

Synthesis and evaluation of new chiral nonracemic C2-symmetric and unsymmetric 2,2′-bipyridyl ligands

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CHEMICAL ANALYSIS; STYRENE; SYNTHESIS (CHEMICAL);

BIPYRIDYL LIGAND; CATALYTICALLY ACTIVE; NMR DATA; POSITIVE OPTICAL ROTATION;

STEREOCHEMISTRY;

EID: 33344466981 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b513286j Document Type: Article

Times cited : (22)

References (29)

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14
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- F. Diederich and P. J. Stang, Wiley-VCH, New York, ch. 4 The corresponding chiral nonracemic unsymmetric 2,2′-bipyridyl ligand (R = i-Pr) was not prepared because of the relatively limited quantity of the chloropyridine acetal 3b (R = i-Pr) at hand as well as in view of the results from the preliminary evaluation of the unsymmetric 2,2′-bipyridyl ligands 2a- b (R = Me and Ph) in copper(i)-catalyzed asymmetric cyclopropanation reactions
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22
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- The enantioselectivity of the reactions were only determined for the major trans-cyclopropane reaction products. The enantiomeric purities of the minor cis-cyclopropane reaction products were not determined as the enantiomers of the corresponding primary alcohol could not be resolved by analytical chiral HPLC (Daicel Chiralcel OD column)
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25
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- note
- Although the corresponding copper(i) triflate complex was not prepared (because of the inherent practical difficulties in handling copper(i) triflate), the copper(i) chloride complex 18 can be considered to be a good model for the actual species that is formed on reduction of the complex formed between the bipyridyl ligand 1c (R = Ph) and copper(ii) triflate with phenylhydrazine. In the cyclopropanation reactions attempted with this ligand, the triflate counterion would also have been displaced from the coordination sphere of the resultant complex

27
- 33344460560
- note
- Of note, when a 2: 1 ratio of ligands 1a- b and copper(ii) triflate were employed in the cyclopropanation reactions the isolated yields of products were lower. This indicated that less of the two catalytically active species [copper(i) triflate and the mono-ligated copper(i) complexes] were present in these instances and that more of the catalytically inactive bis-ligated copper(i) complexes were formed

28
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29
- 33344463518
- note
- Full experimental details regarding the preparation of the 2-chloropyridines acetals 3a- c have been reported (ref. 3,15a)

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