145376-17-6

Upstream product

• 18147-55-2 (E)-crotyltrichlorosilane 
• 100-52-7 benzaldehyde 
• 82238-07-1 2-(methoxymethoxy)-1-phenylbut-3-en-1-ol 
• 1275575-88-6 N,N,N-tributylbutan-1-aminium trifluoro(propa-1,2-dien-1-yl)borate 
• 145332-90-7 (2R,3S)-2-methanol-3-<2-((1-phenyl-1-methoxymethoxy)but-3-en)yloxy>-3,4,5,6-tetrahydro-2H-pyran 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 500757-14-2 C₁₇H₁₆O₃ 
• 81656-05-5 2-methoxy-1-phenylbut-3-en-1-ol 
• 106948-16-7 {Dimethyl-[(R)-1-((S)-phenyl-trimethylsilanyloxy-methyl)-allyl]-silanyl}-diisopropyl-amine 
• 62322-46-7 3-(1-methoxy-1-methylethoxy)prop-1-ene 
• 1208092-25-4 prop-2-ene-1,1-diyl dibenzoate 
• 85677-20-9 threo-1-phenyl-2-(methoxymethoxy)-3-butenol 
• 82238-07-1 erythro-1-phenyl-2-(methoxymethoxy)-3-butenol 

Downstream Products

• 145376-18-7 (4R,5R)-2,2-dimethyl-4-phenyl-5-vinyl-1,3-dioxolane 
• 171736-33-7 Methanesulfonic acid (4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-ylmethyl ester 
• 133269-62-2 (4R,5R)-2,2,4-Trimethyl-5-phenyl-[1,3]dioxolane 
• 133520-57-7 (4S,5R)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-dioxolane 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 473980-94-8 (Z)-(5R,6S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-5,6-dihydroxy-7-phenyl-hept-2-enoic acid methyl ester 
• 473980-95-9 (R)-6-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2-phenyl-ethyl]-5,6-dihydro-pyran-2-one 
• 473980-93-7 (2Z,5E)-(S)-7-(tert-Butyl-dimethyl-silanyloxy)-7-phenyl-hepta-2,5-dienoic acid methyl ester 
• 473980-92-6 (Z)-(5R,6S,7R)-7-Acetoxy-5,6-dihydroxy-7-phenyl-hept-2-enoic acid methyl ester 
• 473980-86-8 (Z)-(5R,6S,7R)-5,6,7-Trihydroxy-7-phenyl-hept-2-enoic acid methyl ester 
• 473980-91-5 (2Z,5E)-(S)-7-Acetoxy-7-phenyl-hepta-2,5-dienoic acid methyl ester 
• 473980-85-7 (2Z,5E)-(S)-7-Hydroxy-7-phenyl-hepta-2,5-dienoic acid methyl ester 
• 96422-53-6 (6R,7R,8R)-goniodiol-7-monoacetate 
• 146236-73-9 (+)-goniodiol 

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.

Enantioselective syn- and anti-Alkoxyallylation of Aldehydes via Br?nsted Acid Catalysis

A diastereo- and enantioselective alkoxyallylation via phosphoric acid catalysis was reported. Under the developed conditions, either 1,2-syn- or 1,2-anti-alkoxyallylation adducts were obtained in good yields with high enantioselectivities.

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.

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.

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

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

A short and general approach to the synthesis of styryllactones: (+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone

(+)-Goniodiol, its acetates and β-trifluoromethyl derivative, (+)-7-epi-Goniodiol and (+)-9-deoxygoniopypyrone, the representatives of styryllactones have been synthesized in a short and general way. The key steps involve the regioselective asymmetric dihydroxylation and the palladium-catalyzed cross-coupling of cyclic allylic carbonate with vinyltributylstannane.

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

Chiral γ-(tetrahydropyranyloxy)allylstannane: a new chiral reagent for the asymmetric synthesis of syn 1,2-diols

(2R,3S)-3-Allyloxy-3,4,5,6-tetrahydro-2H-pyran-2-methanol was prepared in high yield from tri-O-acetyl-D-glucal, an easily available and cheap chiral source.The hydroxy group was protected as the t-butyldiphenylsilyl ether, and the allyl group was converted to the corresponding allyl stannane via formation of allyl carbanion and subsequent trapping with tributylstannyl chloride.The γ-alkoxy allyl stannane 1 bearing the (2R,3S)-2--3,4,5,6-tetrahydro-2H-pyran-3-yloxy auxiliary at the allyl terminus was prepared by this procedure.The reaction of 1 with aldehydes in the presence of AlCl3*OEt2 or AlCl3 gave the corresponding syn adducts 2 with high diastereoselectivities; the ratio of syn/anti > 97:3.The diastereomeric excess of the syn adducts 2, that is, the ratio 2/(2 + the (S,S) isomer of 2), varied from 85 to 94percent.Removal of the protecting group of 2 gave the (R,R) diols 3.The high diastereo- and enantioselectivity in the formation of the (R,R) isomer is accounted for by an anti S'E transition state 18. allylstannane / γ-alkoxyallylstannane / asymmetric synthesis / syn-1,2-diol / Lewis acid / allylstannane-aldehyde condensation / γ-(tetrahydropyranyloxy)allylstannane / anti S'E

Asymmetric Synthesis of Syn 1,2-Diols via the Reaction of Aldehydes with Chiral γ-(Tetrahydropyranyloxy)allylstannanes

Asymmetric synthesis of syn 1,2-diols 3 has been accomplished via the reaction of the chiral γ-alkoxy-substituted allylstannane 1 with aldehydes in the presence of AlCl3 or AlCl3*OEt2, followed by a five-step operation to remove the chiral auxiliary.