135414-96-9

Upstream product

• 100-52-7 benzaldehyde 
• 106948-24-7 (allyl)(diisopropylamino)dimethylsilane 
• 1208092-25-4 prop-2-ene-1,1-diyl dibenzoate 
• 1178609-29-4 (1R,2R,4'R,5'R)-2-[4',5'-bis(methoxydiphenylmethyl)-1',3',2'-dioxaborolan-2'-yl]-1-phenylbut-3-en-1-ol 
• 167967-34-2 C₉H₁₇BO₂ 
• 1329020-18-9 C₁₃H₁₉BO₂ 
• 1329020-55-4 C₁₃H₁₉BO₂ 
• 169517-16-2 2-allenyl-[1,3,2]-dioxaborinane 
• 82238-07-1 erythro-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 85677-20-9 threo-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 106948-16-7 {Dimethyl-[(R)-1-((S)-phenyl-trimethylsilanyloxy-methyl)-allyl]-silanyl}-diisopropyl-amine 
• 81656-05-5 2-methoxy-1-phenylbut-3-en-1-ol 
• 500757-14-2 C₁₇H₁₆O₃ 
• 135414-98-1 B-<3-((diisopropylamino)dimethylsilyl)allyl>diisopinocampheylborane 

Downstream Products

• 155749-26-1 [(4R,5S)-2,2-dimethyl-5-phenyl[1,3]dioxolan-4-yl]methanol 
• 646995-81-5 (4S,5R)-2,2-dimethyl-4-phenyl-5-ethenyl[1,3]dioxolane 

Relevant academic research and scientific papers

3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions

This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.

Enantio- and diastereoselective synthesis of (E)-1,5-syn-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

A highly stereoselective synthesis of (E)-1,5-syn-diols 6 is described. The kinetically controlled hydroboration of allenyltrifluoroborate 8 with Soderquist borane 2 provides the (Z)-allylic trifluoroborate 9, which undergoes sequential allylboration with two different aldehydes to provide (E)-1,5-syn-diols 6 in 72-98% yields with >95% ee and >20:1 dr. Application of this method to the synthesis of the tetrafibricin C(23)-C(40) fragment 19 is described.

Development of a double allylboration reagent targeting 1,5-syn-(E)-diols: Application to the synthesis of the C(23)-C(40) fragment of tetrafibricin

Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42, and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% ee), diastereoselectivity (dr >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.

Diastereo- and enantioselective anti-alkoxyallylation employing allylic gem-dicarboxylates as allyl donors via iridium-catalyzed transfer hydrogenation

(Chemical Equation Presented) Enantioselective transfer hydrogenation of gem-dibenzoate 1e in the presence of aromatic, α,β-unsaturated, or aliphatic aldehydes 2a-i mediated by isopropyl alcohol and employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid, and (R)-SEGPHOS delivers products of alkoxyallylation 3a-i, 4a, 4e, 4f, and 4i in good isolated yields (62-82%) with good to excellent diastereoselectivities (7:1 to 18:1 dr) and exceptional enantioselectivities (90-99% ee). This protocol provides an alternative to the use of premetalated nucleophiles in carbonyl alkoxyallylation. Copyright

Palladium-catalyzed synthesis of enantiomerically pure α-substituted allylboronic esters and their addition to aldehydes

Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl2 to obtain enantiomerically pure α-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.

3-bromozinc propenyl esters: An experimental and theoretical study of the unique stereocrossover observed in their addition to aromatic and aliphatic aldehydes

(Chemical Equation Presented) We report the results of a combined experimental and theoretical study on the reaction of 3-bromopropenyl acetate in the presence of zinc with three different aldehydes (i.e., benzaldehyde, 2-methylpropanal, and cyclohexaneca

Revision of stereochemical assignments of (2,2-dimethyl-5-phenyl-[1,3] dioxolan-4-yl)-methanol

Opposite signs of specific rotation are reported in the literature for (4S,5S)-(2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-methanol. The correct assignment was made by unambiguous synthesis of the title compound via the reaction of (S)-O-TBS-mandelic aldeh

A new protocol for the acetoxyallylation of aldehydes mediated by indium in THF

matrix presented A new precursor of a formal 1-hydroxy allyl anion is represented by 3-bromo-1-acetoxy-1-propene, which is synthesized by the ZnCl2-catalyzed addition of acetyl bromide to propenal. 3-Bromo-1-acetoxy-1-propene reacts with indium

Synthetic Studies on Calyculin A: A Convenient Asymmetric Synthesis of anti-Vicinal Diols

anti-Vicinal diols have been prepared with excellent relative and absolute stereocontrol via the reaction of aldehydes with B-allyl>diisopinocampheylborane in THF and diethyl ether and work-up using potassium fluoride,