53422-64-3

Upstream product

• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 5693-99-2 cis-3-phenyloxirane-2-carboxaldehyde 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 5693-99-2 (±)-3-phenyloxirane-2-carbaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 344423-33-2 2-((Z)-2-Bromo-vinyl)-3-phenyl-oxirane 

Relevant academic research and scientific papers

Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

The versatility of α-chloropropargyl phenyl sulfide affords high stereo- and regioselectivities in indium-promoted coupling reactions under mild conditions

Coupling reactions between α-chloropropargyl phenyl sulfide (11) and a series of aldehydes under aqueous conditions are reported. Not only is good stereoselectivity observed between syn and anti isomeric products, but excellent regioselectivity is also witnessed. In reactions using indium metal as a promoter, the propargyl functionality (12) is retained, unlike the use of more traditional metals that result in formation of products containing a mixture of both propargyl (12) and allene (13) moieties. The reaction is postulated to proceed via either a chelated or nonchelated route, controlled by the presence or absence of indium (111) chloride, and may be used to create synthetically useful building blocks. The formation of epoxyalkyne (14) molecules, which are found in many natural products and have wide use as synthetic templates, is presented as one example.

Preparation of propargylic carbenoids and reactions with carbonyl compounds - A stereoselective synthesis of propargylic halohydrins and oxiranes

The preparation and the reactivity of the zincioallene 3 is described, This organometallic compound reacts with aldehydes to yield propargylic halohydrins with good diastereoselectivities. These halohydrins can easily be converted into propargylic oxirane

Reactivite chimique et thermique d'epoxydes vinyliques halogenes. Synthese d'epoxydes acetyleniques.

1-Alkynyloxiranes 9-15 have been prepared from β-bromovinyloxiranes 1a-7a by phase transfer dehydrohalogenation with aqueous sodium hydroxide/methylene chloride.In the same way β,β-dichlorovinyloxiranes 4c, 5c and 7c led to 1-chloroalkynyloxiranes 16-18.M