66050-98-4

Upstream product

• 4536-23-6 2-methylhexanoic acid 
• 64299-58-7 (E)-2-methyl-2-hexenal 
• 85165-53-3 (2S,3S)-3-Methyl-heptane-1,2-diol 
• 49642-51-5 (S)-(+)-2-methylhexanoic acid 
• 592-41-6 1-hexene 
• 75-24-1 trimethylaluminum 
• 41692-46-0 ethyl 2-methylhexanoate 
• 617-86-7 triethylsilane 
• 775-12-2 diphenylsilane 
• 91177-72-9 (2S,3R)-heptane-2,3-diol 
• 946408-99-7 (2R)-1-tert-butyldiphenylsilyloxy-2-methyl-hexane 
• 296241-81-1 (4R,5R)-2-((1S,2R)-2-Butyl-cyclopropyl)-4,5-bis-(methoxy-diphenyl-methyl)-[1,3,2]dioxaborolane 
• 141022-82-4 (S)-(+)-4-isopropyl-3-hexanoyl-2-oxazolidinone 
• 143965-32-6 (4S)-3-hexanoyl-4-(phenylmethyl)-1,3-oxazolidin-2-one 

Downstream Products

• 1337552-69-8 C₄₂H₈₀O₅Si₃ 
• 1337552-79-0 C₄₂H₈₂O₅Si₃ 
• 1337552-81-4 C₃₆H₆₈O₅Si₂ 
• 1337552-82-5 C₃₆H₇₀O₅Si₂ 
• 1337552-55-2 C₃₉H₇₄O₅Si₂ 
• 66050-82-6 (2R)-methylhexyl (S)-α-methoxy-α-trifluoromethylphenylacetate 
• 97424-48-1 (S)-1-bromo-2-methylhexane 
• 1116651-79-6 (4S,5R)-4-methyl-2-((R)-2-methylhexylselanyl)-5-phenyl-4,5-dihydrooxazole 
• 73376-35-9 (+)-Pumiliotoxin 251D 
• 177767-29-2 (3(2S,4R)4R)-3-(2,4-dimethyloctanoyl)-4-benzyl-2-oxazolidinone 

Relevant academic research and scientific papers

Synthesis and Absolute Configuration of Natural 2-Pyrones

2-Pyrones are frequently produced by microorganisms and often exhibit interesting bioactivities. Therefore, a short and easy synthetic access to these natural products is desirable. Synthetic routes to nectriapyrone, gibepyrone A, racemic gulypyrone A, (+)-germicidin C, (ent)-desoxygermicidin C and (ent)-prolipyrone A via a modular approach are presented, allowing the assignment of the absolute configurations of the latter three chiral compounds. The method failed for the synthesis of (ent)-phomapyrone B that was thus synthesized via a different route, resulting in an assignment of the absolute configuration of natural phomapyrone B.

Catalytic Reductive Pinacol-Type Rearrangement of Unactivated 1,2-Diols through a Concerted, Stereoinvertive Mechanism

A catalytic pinacol-type reductive rearrangement reaction of internal 1,2-diols is reported herein. Several scaffolds not usually amenable to pinacol-type reactions, such as aliphatic secondary–secondary diols, undergo the transformation well without the need for prefunctionalization. The reaction uses a simple boron catalyst and two silanes and proceeds through a concerted, stereoinvertive mechanism that enables the preparation of highly enantiomerically enriched products. Computational studies have been used to rationalize the preference for migration over direct deoxygenation.

Advances and Setbacks in the Total Synthesis of the Fungal Metabolite Curvicollide C: Synthesis and Elaboration of Non-Aldol Stereotriads from Gosteli-Type Allyl Vinyl Ethers

Advances and setbacks are reported in regard to the asymmetric total synthesis of the fungal metabolite curvicollide C relying on a synthetic strategy that exploits non-aldol stereotriads as chiral building blocks. A catalytic asymmetric Gosteli-Claisen rearrangement, a two-step aldehyde-to-alkyne-homologation, and a Julia-Kocienski olefination served as key C/C-connecting transformations.

A facile asymmetric synthesis of (S)-14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth

An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. The target molecule was synthesized in six linear steps and in 30.3% overall yield from commercially available hexanoyl chloride, (S)-4-benzyloxazolidin-2-one and 1,9-nonanediol. The hexanoyl chloride was connected with (S)-4-benzyloxazolidin-2-one, and with the induction of the chiral oxazolidinone auxiliary, after chiral methylation, LAH reduction and then tosylation gave the chiral key intermediate 5 in high stereoselectivity. 1,9-Nonanediol, was selectively brominated, THP protected and subjected to Li2CuCl4-mediated C-C coupling to afford a C12 intermediate. The target molecule, (S)-14-methyl-1-octadecene, was obtained after the two parts were subjected to a second Li 2CuCl4-mediated C-C coupling. Our synthetic approach represents the first time a substrate-control asymmetric synthesis of (S)-14-methyl-1-octadecene has been reported.

Stereochemical investigations reveal the mechanism of the bacterial activation of n-alkanes without oxygen

Anaerobic growth of the bacterium strain HxN1 with n-hexane gives nearly equal amounts of (2R,1 R)- and (2S,1 R)-(1-methylpentyl)succinate, which are formed by the radical addition of the hydrocarbon to fumarate (see scheme). The highly selective attack on the pro-S hydrogen atom at C2 of n-hexane is associated with inversion of the configuration at C2 during binding to fumarate and exhibits isotopic discrimination against a C-2H bond. Copyright

Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters

α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright

LIGANDS FOR SELECTIVE ASYMMETRIC HYDROFORMYLATION

In an aspect, the invention provides compounds of the formula 4: wherein the constituent variables are defined herein.

Convergent enantioselective syntheses of two potential C25-C40 subunits of (-)-caylobolide A

The convergent syntheses of two possible diastereomers of the C25-C40 subunit resident in (-)-caylobolide A have been accomplished. The key reaction featured a chemoselective Ru-catalyzed cross-metathesis between a fully elaborated type I and two function

Enantioselectivity of chiral zirconocenes as catalysts in alkene hydro-, carbo- and cycloalumination reactions

The enantioselectivity of chiral Zr catalysts L1L2ZrCl2 [L1 = L2 = 1-neomenthylindenyl (Ind*), 1; L1 = Cp, L2 = Ind* 2; L1 = Cp, L2 = 1-neomenthylindenyl-4,5,6,7-tetrahydroindenyl (Cp*) 3] in the hydro-, carbo- and cycloalumination of alkenes by organoaluminium compounds (OAC) (AlMe3, AlEt3, HAlBu2i) has been studied. It was found that OAC exhibit the most effect on the reaction chemo- and enantioselectivity. The reaction chemo- and enantioselectivity depend on the catalyst structure and reaction conditions (solvent type, catalyst concentration, temperature) as well. It is shown that the lack of asymmetric induction in the reaction of α-methylstyrene hydroalumination by HAlBu2i, catalyzed with complexes 1 or 3, is the result of the formation of Zr hydride complexes of different structures as reaction intermediates. MTPA was used as a derivatization reagent for the enantiomeric excess estimation and absolute configuration assignment of β-chiral alcohols obtained after the oxidation and hydrolysis of the reaction products. The applicability of MTPA for the assignment of the absolute configuration of the stereogenic centre in β-ethyl substituted primary alcohols and β-alkyl-1,4-butanediols is shown.

Fully reagent-controlled asymmetric synthesis of (-)-Spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction)

The ZACA reaction has been shown to proceed satisfactorily with internally OH-substituted 1-alkenes, provided that the OH group is unprotected and non-allylic. This reaction was used for reagent-controlled asymmetric construction of 3. Allylic alcohol was