79090-73-6

Upstream product

• 124-13-0 Octanal 
• 53915-69-8 allenyltributylstannane 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 106-96-7 propargyl bromide 
• 50-00-0 formaldehyd 
• 74824-53-6 dec-1-yn-3-ol 
• 69841-61-8 1-(tetrahydro-pyran-2-yloxy)-undec-2-yn-4-ol 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 131141-47-4 C₁₉H₂₇NO₄S 
• 131141-75-8 (4S,5R)-5-Heptyl-4-(1-iodo-vinyl)-3-(toluene-4-sulfonyl)-oxazolidin-2-one 
• 131141-65-6 C₁₉H₂₇I₂NO₄S 
• 131141-54-3 syn-4-acetoxy-3-<(tolylsulfonyl)amino>-2-iodoundecene 
• 131141-66-7 C₁₉H₂₇I₂NO₄S 
• 131141-65-6 C₁₉H₂₇I₂NO₄S 

Relevant academic research and scientific papers

Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.

A general approach to terminal allenols

We have demonstrated a very general method for the preparation of essentially any terminal 2,3-allenol from the corresponding alkynols, which may be easily available from propargylic alcohols by alkylation, or from terminal alkynes by deprotonation and 1,

CuI-catalyzed synthesis of functionalized terminal allenes from 1-alkynes

Relative to our original protocol that uses CuI (0.5 equiv.), paraformaldehyde (2.5 equiv.), and dicyclohexylamine (1.8 equiv.), a facile and efficient protocol for the gram-scale synthesis of functionalized terminal allenes by using CuI (7.5-10 mol-%), p

Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols

A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl- 5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols

(Chemical Equation Presented) A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of γ-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.

Palladium(II)-catalyzed SN2′ reactions of α-allenic acetates. Stereoconvergent synthesis of (Z,E)-2-bromo-1,3-dienes

The reaction of acetylated α-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)2 provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diaste-reoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

Carbonyl propargylation or allenylation by 3-haloprop-1-yne with tin(n) halides and tetrabutylammonium halides

3-Bromoprop-1-yne causes carbonyl propargylation with tin(n) chloride and tetrabutylammonium bromide in water to produce 1-substituted but-3-yn-1-ols, while 3-chloroprop-1-yne causes carbonyl allenylation with tin(II) iodide and tetrabutylammonium iodide in 1,3-dimethylimidazolidin-2-one to produce 1-substituted buta-2,3-dien-1-ols.

Barbier-type allylation of carbonyl compounds and imines with metallic cadmium

Cadmium mediated allylation of a variety of carbonyl compounds and imines in a Cd/Bu4NBr/THF system afforded excellent yields of the corresponding homoallylic alcohols and amines under very mild reaction conditions.

A HIGHLY STEREOSELECTIVE CONVERSION OF α-ALLENIC ALCOHOLS TO 1,2-SYN AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION

The iodocarbamation of α-allenic alcohol O-carbamates is described.Reactions carried out in anhydrous Et2O are highly diastereoselective, providing the cyclic carbamates trans-8 and cis-9 in ratios ranging from 21:1 to >99:1.Hydrolysis and acetylation pr

Selective Propargylation of Carbonyl Compounds with Allenylstannane/Alkyllithium Mixed Reagents

1-Substituted allenyltrialkylstannanes readily undergo transmetalation with an alkyllithium to generate a tetraalkylstannane and an equilibrating mixture of the allenyl- and propargyllithium compounds.The organolithium derivatives react with a variety of aldehydes and ketones at low temperature to give, after aqueous workup, the regioisomeric acetylenic and allenic carbinols in high yields.The degree of the regioselection is highly sensitive to the steric and electronic properties of the carbonyl substrates.Excellent acetylene selectivities are obtainable by combination of the bulky reagents and substrates or by using acylsilanes as carbonyl components.The origin of the regioselectivity is discussed.