10544-99-7

Upstream product

• 929-03-3 bromo-penta-2,4-dienyl-zinc 
• 100-52-7 benzaldehyde 
• 40596-30-3 (E)-1-chloro-2,4-pentadiene 
• 87920-24-9 tributyl(penta-2,4-dienyl)stannane 
• 116997-87-6 ethyl-1,4-pentadien-3-yl carbonate 
• 84568-09-2 trimethyl(2,4-pentadienyl)stannane 
• 922-65-6 divinylcarbinol 
• 102820-40-6 2-(1-ethenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 448235-53-8 ((penta-1,4-dien-3-yloxy)methyl)benzene 
• 52022-82-9 (E)-5-bromopenta-1,3-diene 
• 591-93-5 1,4-Pentadiene 
• 504-60-9 penta-1,3-diene 
• 1001-93-0 1-bromopenta-2,4-diene 

Downstream Products

• 957522-33-7 (3aS,4S,7aR)-2-Ethyl-4-phenyl-5-vinyl-3a,4,7,7a-tetrahydro-isoindole-1,3-dione 

Relevant academic research and scientific papers

Pentadienylzirconium compounds: Easily accessible new reagents for selective pentadienylation reactions

2,4-Pentadienylzirconium complexes are generated from 2,4- or 2,2′-pentadienyl ethers in turn. These compounds react in situ with aldehydes and ketones in a totally γ-regioselective manner and with predominant anti stereoselectivity to produce bis(homoall

High γ-selectivity in the coupling of penta-2,4-dienyl- and pent-2-en-4-ynylindium reagents with aldehydes

A variety of penta-2,4-dienyl- and pent-2-en-4-ynylindium reagents have been prepared in situ from the reaction of the corresponding allylic bromides with indium metal, and their reactions with carbonyl compounds have been examined. The reaction with alde

Asymmetric γ-Selective Pentadienylation of Aldehydes Catalyzed by BINAP·Ag(I) Complex

Reaction of aldehydes with (E)-2,4-pentadienyltributyltin or trimethyltin in the presence of a catalytic amount of BINAP-silver(I) complex affords the corresponding γ-pentadienylated optically active alcohols with high enantioselectivities.

Highly selective and robust palladium-catalyzed carbon-carbon coupling between allyl alcohols and aldehydes via transient allylboronic acids

The highly regio- and stereoselective coupling of allyl alcohols with aldehydes could be achieved with 5 mol-% of SeCSe pincer complex catalyst and p-toluenesulfonic acid in the presence of diboronic acid. The transformations have a broad synthetic scope, and the high yields were obtained without the use of an inert atmosphere and carefully dried solvents. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Cu-Catalyzed Highly Stereoselective Syntheses of (E)-δ-Vinyl-homoallylic Alcohols

Stereoselective synthesis of (E)-δ-vinyl-homoallylic alcohols was developed. Starting from α-vinyl allylboronate, Cu-catalyzed allylation of aldehydes or ketones forms secondary or tertiary δ-vinyl-homoallylic alcohols with high E-selectivities. It is pro

Tetracycline analogues with a selective inhibitory effect on HIF-1α

As part of a programme to discover novel transcription factor inhibitors, a 40-membered library of tetracycline analogues was screened to identify potential HIF-1 inhibitors. Two novel analogues (5b and 5c) with significant HIF-1 modulation properties were identified. These molecules possess good cellular penetration properties, and provide significant down-regulation of VEGF in U251 cells.

Petasis borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. An efficient one-pot route to stereodefined α-amino acids and homoallyl alcohols

An efficient one-pot procedure was designed by integration of the pincer-complex-catalyzed borylation of allyl alcohols in the Petasis borono-Mannich reaction and in allylation of aldehydes and ketones. These procedures are suitable for one-pot synthesis of α-amino acids and homoallyl alcohols from easily available allyl alcohol, amine, aldehyde, or ketone substrates. In the presented transformations, the active allylating agents are in situ generated allyl boronic acid derivatives. These transient intermediates are proved to be reasonably acid-, base-, alcohol-, water-, and air-stable species, which allows a high level of compatibility with the reaction conditions of the allylation of various aldehyde/ketone and imine electrophiles. The boronate source of the reaction is diboronic acid or in situ hydrolyzed diboronate ester ensuring that the waste product of the reaction is nontoxic boric acid. The regio- and stereoselectivity of the reaction is excellent, as almost all products form as single regio- and stereoisomers. The described procedure is suitable to create quaternary carbon centers in branched allylic products without formation of the corresponding linear allylic isomers. Furthermore, products comprising three stereocenters were formed as single products without formation of other diastereomers. Because of the highly disciplined consecutive processes, up to four-step, four-component transformations could be performed selectively as a one-pot sequence. For example, stereodefined pyroglutamic acid could be prepared from a simple allyl alcohol, a commercially available amine, and glyoxylic acid in a one-step procedure. The presented method also grants an easy access to stereodefined 1,7-dienes that are useful substrates for Grubbs ring-closing metathesis.

A consecutive Diels-Alder approach toward a Tet repressor directed combinatorial library

A combinatorial library of 180 tetracycline analogs was generated by solution phase parallel synthesis applying a consecutive Diels-Alder strategy. Chemical methodology suitable for three-dimensional solution phase parallel synthesis was developed that en

Skeletal diversity via a branched pathway: Efficient synthesis of 29 400 discrete, polycyclic compounds and their arraying into stock solutions

We report the synthesis and arraying of 29400 structurally diverse and complex polycyclic carbocycles using diversity-oriented synthesis (DOS) and the "one bead-one stock solution" technology platform. Skeletal diversity, a difficult challenge in DOS, was

Asymmetric addition of allylic stannanes to aldehydes catalyzed by binap·Ag(I) complex

Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP·AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in TI-IF at