Efficient ligands, chiral 2-[2,2-dimethyl-1-(2-pyridyl)propoxy]-1,1-diarylethanols for highly enantioselective addition of alkynylzinc reagents to various aldehydes

Ishizaki, Miyuki; Hoshino, Osamu

doi:10.1016/s0957-4166(00)86262-x

Cited by 89 publications

(22 citation statements)

References 7 publications

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“…1). 13 The sulfamide -amine alcohol binds with Zn in a tridentate fashion. The nitrogen atom from the sulfonamide serves as another weakly coordinative site in the cycle because it …”

Section: Resultsmentioning

confidence: 99%

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Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OⁱPr)₄

Mao¹,

Wan²,

Wu³

et al. 2005

Chirality

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Ephedrine-derived sulfamide-amine alcohol 3 was found to be an effective catalyst for the asymmetric phenylacetylene addition to aldehydes at room temperature without using Ti(O(i)Pr)4 and Zn(OTf)2. It afforded the propargylic alcohols in high yields (up to 99%) and good enantioselectivities (up to 84% ee), which were much higher than that based on N-methylephedrine under the same reaction conditions. Its weakly coordinative sulfonamide moiety of the ligand plays an important role for further acceleration and stereocontrol in the alkynylation.

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“…1). 13 The sulfamide -amine alcohol binds with Zn in a tridentate fashion. The nitrogen atom from the sulfonamide serves as another weakly coordinative site in the cycle because it …”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (CDCl 3 ): d 0.95 -0.98 (m, 6H), 1.65 -1.75 (m, 2H), 1.91 (t, J = 6.8 Hz, 1H), 2.17 (s, 1H), 4.64 (t, J = 7.2 Hz, 1H), 7.28 -7.42 (m, 5H). 13 C NMR (CDCl 3 ): d 22. 67, 22.73, 24.98, 29.85, 47.05, 61.61, 84.89, 90.60, 122.85, 128.45, 131.81.…”

Section: Typical Procedures For Asymmetric Alkynylation Reactionsmentioning

confidence: 99%

Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OⁱPr)₄

Mao¹,

Wan²,

Wu³

et al. 2005

Chirality

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“…[29][30][31][32][33][34][35] Since Ishizaki and Hoshino 24 reported the first addition of alkynylzinc reagents to aldehydes in 1994, some chiral ligands, such as N-methylephedrine, 19 sulfonamide alcohol, 36 BINOL and its derivatives, [20][21][22][23] have successfully been applied to this reaction in recent years. The amino alcohol ligand shows excellent enantioselectivity for the alkynylzinc addition to aliphatic aldehydes, and the BINOL catalyst shows excellent enantioselectivity for the alkynylzinc addition to aromatic aldehydes.…”

Section: Scheme 1 Reported Bifunctional Binol Derivativesmentioning

confidence: 99%

Bifunctional Enantioselective Ligands of Chiral BINOL Derivatives for Asymmetric Addition of Alkynylzinc to Aldehydes

Zou

Zheng

et al. 2008

Chin. J. Chem.

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Four analogous binaphthyl compounds (R)-3a-3d containing (R)-3,3'-bis(2-pyridyl) groups were synthesized by the conjugation of (R)-2,2'-dimethoxy-1,1'-binaphthyl-3,3'-diboronic acid [(R)-2] with 2-bromopyridine, 2-bromo-5-methylpyridine, 2-chloro-4-fluoropyridine and 2-chloro-3-(trifluoromethyl)pyridine via Pd-catalyzed Suzuki reactions, respectively. The application of the four chiral ligands in combination with Et 2 Zn and Ti(Oi-Pr) 4 to the asymmetric addition of phenylacetylene to various aldehydes has been studied. The results show that (R)-3a and (R)-3b are not good catalysts for the alkynylzinc addition to aldehydes, (R)-3d shows good enantioselectivity only for the alkynylzinc addition to aliphatic aldehydes, and (R)-3c exhibits excellent enantioselectivity for phenylethynylzinc addition to both aromatic and aliphatic aldehydes. All the four chiral ligands produced the opposite configuration of the propargylic alcohols to that of the chiral ligands.

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“…Studies have also been carried out with mixed organozinc agents such as ethyl(2-phenylethynyl)zinc (18, Equation 3.10) [33], prepared from reactions between terminal alkynes and Et 2 Zn. The addition of such species to aldehydes was examined in the presence of 10 mol % pyridinyl alcohol ligand 19, with optimal selectivities observed at room temperature [34].…”

Section: Additions With Stoichiometric Amounts Of Metal Acetylidesmentioning

confidence: 99%

Addition of Terminal Acetylides to CO and CN Electrophiles

Aschwanden¹,

Carreira²

2004

Acetylene Chemistry

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Efficient ligands, chiral 2-[2,2-dimethyl-1-(2-pyridyl)propoxy]-1,1-diarylethanols for highly enantioselective addition of alkynylzinc reagents to various aldehydes

Cited by 89 publications

References 7 publications

Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OⁱPr)₄

Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OⁱPr)₄

Bifunctional Enantioselective Ligands of Chiral BINOL Derivatives for Asymmetric Addition of Alkynylzinc to Aldehydes

Addition of Terminal Acetylides to CO and CN Electrophiles

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Efficient ligands, chiral 2-[2,2-dimethyl-1-(2-pyridyl)propoxy]-1,1-diarylethanols for highly enantioselective addition of alkynylzinc reagents to various aldehydes

Cited by 89 publications

References 7 publications

Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OiPr)4

Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OiPr)4

Bifunctional Enantioselective Ligands of Chiral BINOL Derivatives for Asymmetric Addition of Alkynylzinc to Aldehydes

Addition of Terminal Acetylides to CO and CN Electrophiles

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Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OⁱPr)₄

Readily available sulfamide–amine alcohols for enantioselective phenylacetylene addition to aldehydes in the absence of Ti(OⁱPr)₄