33732-63-7

Upstream product

• 859303-44-9 acetic acid-(4-methyl-5-phenyl-tetrahydro-[2]furyl ester) 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 

Downstream Products

• 859445-20-8 2-phenyl-3-methyltetrahydrofuran 
• 1822-41-9 1-Formyl-2-methyl-3-phenyl-cyclopropan 
• 99344-35-1 (2S,3S,4S,5R)-3-Bromo-4-methyl-5-phenyl-tetrahydro-furan-2-ol 
• 99344-44-2 Acetic acid (2R,3S,4S,5R)-3-bromo-4-methyl-5-phenyl-tetrahydro-furan-2-yl ester 
• 112359-39-4 4α,5α-dideuterio 3α-methyl 2β-phenyl tetrahydrofuran 
• 112359-39-4 4β,5β-dideuterio 3α-methyl 2β-phenyl tetrahydrofuran 
• 112359-39-4 4α,5α-dideuterio 3β-methyl 2β-phenyl tetrahydrofuran 
• 24581-87-1 2-methyl-3-phenyl-1-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts

A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.

Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-Allyls

The first enantioselective carbonyl crotylations through direct use of alkynes as chiral allylmetal equivalents are described. Chiral ruthenium(II) complexes modified by Josiphos (SL-J009-1) catalyze the C-C coupling of TIPS-protected propargyl ether 1a with primary alcohols 2a-2o to form products of carbonyl siloxy-crotylation 3a-3o, which upon silyl deprotection-reduction deliver 1,4-diols 5a-5o with excellent control of regio-, anti-diastereo-, and enantioselectivity. Structurally related propargyl ethers 1b and 1c bearing ethyl- and phenyl-substituents engage in diastereo- and enantioselective coupling, as illustrated in the formation of adducts 5p and 5q, respectively. Selective mono-tosylation of diols 5a, 5c, 5e, 5f, 5k, and 5m is accompanied by spontaneous cyclization to deliver the trans-2,3-disubstituted furans 6a, 6c, 6e, 6f, 6k, and 6m, respectively. Primary alcohols 2a, 2l, and 2p were converted to the siloxy-crotylation products 3a, 3l, and 3p, which upon silyl deprotection-lactol oxidation were transformed to the trans-4,5-disubstituted γ-butyrolactones 7a, 7l, and 7p. The formation of 7p represents a total synthesis of (+)-trans-whisky lactone. Unlike closely related ruthenium catalyzed alkyne-alcohol C-C couplings, deuterium labeling studies provide clear evidence of a novel 1,2-hydride shift mechanism that converts metal-bound alkynes to π-allyls in the absence of intervening allenes.

SYNTHESE DE COMPOSES DIHYDRO-2,3 FURANNIQUES PAR HYDROBORATION D'ALCOOLS β-ACETYLENIQUES

Hydroboration of β acetylenic alcohols followed by NaOH/H2O2 oxidation leads to hemiacetals of γ aldols which are easily dehydrated to 2,3-dihydrofuran compounds.The reaction gives good yields with hindered alcohols and its stereochemistry may be controlled during the organometallic synthesis of the starting alcohol.