167611-52-1

Upstream product

• 100-52-7 benzaldehyde 
• 693-02-7 hex-1-yne 
• 693-03-8 n-butyl magnesium bromide 
• 16644-98-7 (E)-1-iodohexene 
• 37609-12-4 (E)-hex-1-enyldicyclohexylborane 
• 91083-28-2 (E)-2-(1-hexenyl)-1,3,2-dioxaborinane 
• 21915-53-7 (2R,3S)-(3-phenyloxiran-2-yl)methanol 
• 5693-99-2 (2S,3S)-3-phenyloxirane-2-carbaldehyde 

Relevant academic research and scientific papers

One-pot asymmetric synthesis of acyclic chiral epoxy alcohols via tandem vinylation - Epoxidation with dioxygen

(Chemical Equation Presented) We have developed a one-pot procedure for the asymmetric synthesis of a synthetically challenging class of acylic secondary epoxy alcohols with three contiguous stereocenters from simple achiral starting materials. The epoxy alcohols are synthesized via a tandem catalytic asymmetric vinylation of an aldehyde coupled with a diastereoselective epoxidation reaction. A vinylzinc reagent generated in situ undergoes enantioselective addition to an aldehyde in the presence of a zinc catalyst to provide an allylic zinc alkoxide. This species is then epoxidized by addition of dioxygen and a titanium tartrate catalyst to give epoxy alcohols with excellent enantioselectivities, in most cases, and with diastereoselectivities up to 4.5:1 in favor of the threo-diastereomer. The system described herein represents a significant advance in terms of synthetic efficiency and selectivity.

A convenient, one-step synthesis of optically active tertiary aminonaphthol and its applications in the highly enantioselective alkenylations of aldehydes

Optically active tertiary aminonaphthol 1 was obtained by a new, convenient procedure and was found to catalyze the enantioselective alkenylation of various aldehydes with high ee values, which provides a practical method for the synthesis of chiral (E)- allyl alcohols.

A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes

Asymmetric allylation and vinylation of aldehydes with allyl halides and vinyl halides have been achieved using the chromium(II)-oxazoline catalyst. The catalyst promotes the highly efficient enantioselective Nozaki–Hiyama-Kishi (NHK) allylation of aldehydes using allyl bromide, producing the corresponding homoallylic alcohols in good yields (up to 84%) and a high level of enantioselectivity (up to 98% ee). Meanwhile, the NHK vinylation of aldehydes produce desired allylic alcohols in satisfactory yields (up to 88%) and a high level of enantioselectivity (up to 97% ee). We developed a reliable and milder protocol for preparing chiral homoallylic and allylic alcohols.

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Enantioselective addition of alkenylzinc reagents to aldehydes with organoboronates as the alkenyl source

Alkenylboronates were used as a vinyl source in the asymmetric addition of an alkenylzinc reagent to aldehydes catalyzed by a dendritic ligand. The resulting allylic alcohol products were obtained in 66-96% ee and 35-64% yields.

Highly enantioselective synthesis of (E)-allylic alcohols

(Chemical Equation Presented) The asymmetric addition of alkenylzincs to aromatic and a-branched aliphatic aldehydes catalyzed by 1 generated the corresponding (E)-allylic alcohols with >95% ee and good to excellent chemical yields, especially >99.5% ee w

Aziridine-modified amino alcohols as efficient modular catalysts for highly enantioselective alkenylzinc additions to aldehydes

N-Tritylaziridino alcohols have been easily synthesized in a straightforward synthetic route from an inexpensive and easily available chiral pool. They were used in the enantioselective alkenylzinc additions to aldehydes furnishing the products in excelle

A positional scanning approach to the discovery of dipeptide-based catalysts for the enantioselective addition of vinylzinc reagents to aldehydes

A combinatorial library of dipeptide N-acylethylenediamine-based ligands was synthesized by parallel solid-phase methods. These ligands were screened in crude form as catalysts for the asymmetric addition of vinylzinc reagents to aldehydes to give chiral allylic alcohols. Three sites of diversity on the ligands were optimized using a positional scanning approach. The optimized structure from the library, ligand 54, was found to catalyze the formation of 10 different (E)-allylic alcohols with enantioselectivities ranging from 90% to 95% ee. This ligand was effective for both aromatic and α-branched aldehydes, and vinylzinc reagents derived from both bulky and straight chain terminal alkynes.

New β-amino thiols as efficient catalysts for highly enantioselective alkenylzinc addition to aldehydes

A series of new optically active β-amino thiols and thiolacetates prepared from the simple natural amino acid, (S)-(-)-valine, were found to be effective catalysts for the enantioselective addition of alkenylzinc to aldehydes and thereby providing an effi

Enantioselective addition of vinylzinc reagents to aldehydes catalyzed by modular ligands derived from amino acids

A series of N-acylethylenediamine-based ligands were synthesized from Boc-protected amino acids. The ligands were screened for the ability to catalyze the asymmetric addition of vinylzinc reagents to aldehydes. Three sites of diversity on the ligands were optimized for this reaction using a positional scanning approach. The optimized ligand 3d was found to catalyze the formation of 15 different (E)-allylic alcohols with enantioselectivities that ranged from 52 to 91% ee and yields that ranged from 40 to 90%. This ligand was especially effective for the reaction of aromatic aldehydes with vinylzinc reagents derived from bulky terminal alkynes. Ligand 3d catalyzed the addition of (E)-(3,3-dimethylbut-1-enyl)(ethyl)zinc to 2-naphthaldehyde to give (R,E)-4,4-dimethyl-1-(naphthalene-1-yl)pent-2-en-1-ol in 89% ee. The ee of this product could be increased to 97% through a single recrystallization.