68972-96-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 5607, 1995 DOI: 10.1016/0040-4039(95)01073-Q

InChI:InChI=1/C18H20O2/c1-3-9-17(10-4-1)15-19-13-7-8-14-20-16-18-11-5-2-6-12-18/h1-12H,13-16H2/b8-7-

Upstream product

• 1476-11-5 Z-1,4-dichlorobutene 
• 100-51-6 benzyl alcohol 
• 6117-80-2 1,4-butenediol 
• 100-39-0 benzyl bromide 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 100-44-7 benzyl chloride 
• 162369-37-1 2,3-bis((benzyloxy)methyl)thiirane 
• 93877-21-5 1,4-dibenzyloxybut-2-yne 
• 136458-56-5 2,3-bis((benzyloxy)methyl)oxirane 
• 14593-43-2 benzyl allyl ether 
• 70677-94-0 1,4-di(benzyloxy)but-2,3-ene 
• 68973-05-7 (2R*,3S*)-2,3-bis((benzyloxy)methyl)oxirane 
• 98-88-4 benzoyl chloride 

Downstream Products

• 60656-87-3 benzyloxyacetoaldehyde 
• 132487-15-1 1-(t-2,t-3-dihydroxymethyl-r-1-cyclopropyl)thymine 
• 132487-14-0 9-(t-2,t-3-dihydroxymethyl-r-1-cyclopropyl)-9H-adenine 
• 68973-05-7 (2R*,3S*)-2,3-bis((benzyloxy)methyl)oxirane 
• 25260-60-0 cis-1,4-bis(acetyloxy)but-2-ene 
• 100-44-7 benzyl chloride 
• 431-03-8 dimethylglyoxal 
• 134692-47-0 (Z)-4-(benzyloxy)-2-butenyl acetate 
• 136458-56-5 2,3-bis((benzyloxy)methyl)oxirane 
• 87172-27-8 cis-4-benzyloxy-2,3-epoxy-1-butanol 
• 1262957-89-0 C₁₉H₂₀O₂S 
• 342651-74-5 N-(2-(1-benzyloxy)propylidene)-2-methylpropanesulfinamide 

Relevant academic research and scientific papers

Copper(0) nanoparticle catalyzed Z-Selective Transfer Semihydrogenation of Internal Alkynes

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SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

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Correction to: Nickel-catalyzed asymmetric reductive cross-coupling to access 1,1-diarylalkanes (Journal of the American Chemical Society (2017) 139 (5684-5687) DOI: 10.1021/jacs.7b01705)

Pages 5684 and 5685, Table of Contents, and Supporting Information. The stereochemistry of L1, depicted as the (S,S)- enantiomer in Figure 1, Table 1, the TOC graphic (identical to Figure 1), and the Supporting Information of the original publication, was incorrect. (R,R)-L1 was used in this study. The stereochemistry of (R,R)-L1 has been confirmed by singlecrystal X-ray diffraction; the X-ray diffraction data and CIF file for (R,R)-L1 have been added to the Supporting Information. The corrected TOC graphic/Figure 1 is shown here. (R,R)-L4 and (R,R)-L5 were also used in Table 1 and incorrectly depicted as (S,S)-L4 and (S,S)-L5 in the original publication. To reflect that different enantiomeric series of catalysts were used, Table 1 has been updated to indicate that entries 2, 3, and 6 produce (S)-3a. This correction does not change the stereochemical assignment of the diarylalkane products, or the conclusions of the Communication. The stereochemistry of the products was assigned by obtaining an X-ray structure of diarylalkane 3k, and the rest of the compounds were assigned by analogy. (Table Presented).

Solid supported Hayashi–J?rgensen catalyst as an efficient and recyclable organocatalyst for asymmetric Michael addition reactions

A comparison of three different catalytic systems for the efficient, asymmetric synthesis of N-({(3R,4R)-4-[(benzyloxy)methyl]pyrrolidin-3-yl}methyl)-N-(2-methylpropyl)benzenesulfonamide 1 (BZN) is described. The presented strategy is based on the organocatalytic Michael addition of aldehyde 2 to trans-nitroalkene 3, and subsequent reductive cyclization. High yields, enantio-, and diastereoselectivities were achieved in the Michael addition by application of a POSS- or Wang resin-supported Hayashi–J?rgensen catalyst.

Total Synthesis of Ovafolinins A and B: Unique Polycyclic Benzoxepin Lignans through a Cascade Cyclization

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Total synthesis of (-)-bicubebin A, B, (+)-bicubebin C and structural reassignment of (-)-cis-cubebin

The first total synthesis of (-)-bicubebin A, and two previously unreported dilignans, (-)-bicubebin B and (+)-bicubebin C has been achieved through the dimerization of (-)-cubebin, confirming the structure and absolute stereochemistry of (-)-bicubebin A. Analysis of the data for (-)-bicubebin B showed it matched that of reported compound (-)-cis-cubebin. The NMR data of the subsequently synthesized proposed structure of cis-cubebin confirmed that its original proposed structure was incorrect.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling to Access 1,1-Diarylalkanes

An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, indoles, and piperidines.