145376-18-7

Upstream product

• 82238-14-0 (1R,2R)-2-(1-Methoxy-1-methyl-ethoxy)-1-phenyl-but-3-en-1-ol 
• 19261-14-4 1-phenylbut-3-ene-1,2-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 100-52-7 benzaldehyde 
• 77896-99-2 2-<(Z)-3-(1-methoxy-1-methylethoxy)-2-propenyl>-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 145332-90-7 (2R,3S)-2-methanol-3-<2-((1-phenyl-1-methoxymethoxy)but-3-en)yloxy>-3,4,5,6-tetrahydro-2H-pyran 
• 145376-17-6 (1R,2R)-1-phenyl-but-3-ene-1,2-diol 
• 104516-09-8 1-phenylbuta-2,3-dien-1-ol 

Downstream Products

• 133520-57-7 (4S,5R)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-dioxolane 
• 133269-62-2 (4R,5R)-2,2,4-Trimethyl-5-phenyl-[1,3]dioxolane 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 

Relevant academic research and scientific papers

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.

3-Bromopropenyl esters in organic synthesis: Indium- and zinc-mediated entries to alk-1-ene-3,4-diols

Metallic indium and zinc readily add to 3-bromopropenyl acetate (5) and benzoate (6) either in THF or in water, affording the corresponding 3-acyloxyallyl organometallic compounds. Nucleophilic addition to aldehydes opens a route to alk-l-ene-3,4-diols 2 in good to excellent yields. Two synthetic protocols were developed, the former involving indium in THF under Grignard conditions and the latter involving zinc in aqueous ammonium chloride under Barbier conditions. The diastereo-selectivity, under all the conditions examined, mainly depends on the nature of the carbonyl compound; conjugated aldehydes afford syn adducts 2, while unconjugated aldehydes display the opposite anti stereopreference.

Total synthesis of (±)-9-deoxygoniopypyrone. Application of the iodocyclofunctionalization reaction of α-allenic alcohol derivatives

The synthesis of (±)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 5 is described. Iodocyclofunctionaliztion of the N-tosyl carbamate derivative of 5 using I2 and Ag2CO3 provided, in a highly diastereoselective and r

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

Total Synthesis of (+/-)-9-Deoxygoniopypyrone

The total synthesis of (+/-)-9-deoxygoniopypyrone (1) from the α-allenic alcohol 2 is described.The synthesisis accomplished in 10 steps with the relative configuration of the three contiguous asymmetric centers being established by the highly diastereose

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.

Stereoselective Synthesis of Alcohols, XX. - Diastereoselective Addition of γ-Alkoxyallylboronates to Aldehydes

Both the (Z)- and (E)-γ-alkoxysubstituted allylboronates 1 and 3 have been prepared.They add to aldehydes with a diastereoselectivity generally exceeding 90percent to give the syn-(2) and anti-diol derivatives 4, respectively.The structure of one of these adducts has been established by conversion into exo-brevicomin (26).