69248-81-3

Upstream product

• 109279-76-7 (R)(S)-1-bromo-4,4-dimethyl-1,2-pentadiene 
• 591-50-4 iodobenzene 
• 78389-91-0 4,4-dimethyl-1,2-pentadienylzinc chloride 
• 79754-98-6 C(CH₃)3HCCCHCu 
• 81363-97-5 C₇H₁₁Ag 
• 213193-36-3 {2-Hydroxy-3,3-dimethyl-1-[1-phenyl-meth-(E)-ylidene]-butyl}-phosphonic acid diethyl ester 
• 132350-97-1 4,4-dimethyl-1-phenyl-pent-1-yn-3-ol 
• 630-19-3 pivalaldehyde 
• 536-74-3 phenylacetylene 
• 5362-74-3 pivalaldehyde N-tosylhydrazone 
• 1078-58-6 diphenylzinc 
• 100207-07-6 (R)-1-bromo-4,4-dimethyl-1,2-pentadiene 
• 677-22-5 tert-butylmagnesium chloride 
• 4192-77-2 ethyl cinnamate 

Downstream Products

• 113120-87-9 C₂₆H₂₄OS 
• 113120-88-0 3-tert-Butyl-2-[1-phenyl-meth-(Z)-ylidene]-3,11b-dihydro-2H-7-oxa-1-thia-benzo[de]anthracene 
• 113120-86-8 C₂₆H₂₄OS 

Relevant academic research and scientific papers

STEREOCHEMISTRY OF THE Pd(PPh3)4-CATALYZED CONVERSION OF 1-BROMOALLENES INTO PHENYL SUBSTITUTED ALLENES.

1-Bromoallenes 1 are converted into the phenyl substituted allenes 2 with inversion of configuration in the allenyl moiety by reaction with Ph2Zn using Pd(PPh3)4 as catalyst.

Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes

A new and facile one-pot synthesis of 1,3-disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up t

A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes

Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is

CuI-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes: Synthesis of 1,3-disubstituted allenes

A CuI-catalyzed synthesis of 1,3-disubstituted allenes from 1-alkynes by the reaction with various N-tosylhydrazones has been developed. This method, which uses readily available starting materials and is operationally simple, offers 1,3-disubstituted all

Stereoretentive suzuki-miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-Peridinin

Stimulated by the substantial challenge of synthesizing the complex and sensitive stereogenic allene-containing core of (-)-peridinin, the first stereocontrolled coupling of haloallenes with boronic acids has been achieved. This new method and the principles that emerged during its development stand to enable the more efficient and flexible preparation of a wide range of natural products, pharmaceuticals, and intermediates that possess a stereogenic allene motif. This new reaction was harnessed to achieve the first completely stereocontrolled total synthesis of (-)-peridinin. This synthesis was accomplished using only one reaction iteratively to assemble four fully functionalized building blocks with complete stereoretention at each initial halide or boron-bearing carbon. This synthesis elevates the capacity of the iterative cross-coupling strategy to an unprecedented benchmark. Moreover, the efficient and highly modular nature of this synthesis promises to enable systematic dissection of the heretofore enigmatic structure/function relationships that underlie the protein-like antilipoperoxidant activities of this remarkable small molecule natural product.

Silver(i)-mediated highly enantioselective synthesis of axially chiral allenes under thermal and microwave-assisted conditions

Silver(i) salts mediated stereospecific transformation of optically active propargylamines to axially chiral allenes with excellent enantioselectivities (17 examples with 96-99% ee; one substrate with 91% ee) without subsequent racemization.

Stereoselective synthesis of chiral 3-aryl-1-alkynes from bromoallenes and heterocuprates

The synthesis of chiral 3-aryl-1-alkynes 3 via cross-coupling of 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes 1 and arylbromocuprates (RCuBr)MgBr-LiBr 2 was examined. With phenylcopper reagents and its para-substituted derivatives, as well as with 2-naphth

Asymmetric dihydroxylation of disubstituted allenes

Asymmetric dihydroxylation of 1,1-disubstituted and 1,3-disubstituted allenes can be used to synthesize chiral α-hydroxy ketones. We have also obtained α,α′-dihydroxy ketones with high enantioselectivity from 1,3-disubstituted allenes. Low conversion of the dihydroxylation of chiral allenes can be used as a kinetic resolution of sterically hindered allenes.

Synthesis of allenes by double Horner-Wadsworth-Emmons reaction

LDA treatment of aldehydes or ketone with alkenylphosphonates 2, prepared by Horner-Wadsworth-Emmons (HWE) reaction of methylenebisphosphonate 1 with aldehydes, afforded Baylis-Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided allenes in good yields. One-flask procedure was successfully developed starting from 1 to afford an allene in a reasonably good yield.

Allenes through Horner-Wadsworth-Emmons olefination of alkenylphosphonates

Mono- and di-substituted allenes 5 were synthesized by successive Horner-Wadsworth-Emmons olefination starting from methylene-bisphosphonate 1 and two carbonyl compounds. The key to success is KH or KH-18-crown-6 as a base for the second HWE olefination o