167777-84-6

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 170028-87-2 D-xylose-(2R,3R,4R)-5-di-O-isopropylidene-[4-(methylphenyl)sulfonyl]hydrazone 
• 668441-11-0 2-phenyl-3-[(1'S,2'R)-1'-(2',3'-O-isopropylidene-1',2',3'-trihydroxypropyl)]-5,6-dihydro-1,4-dithiin 
• 591-50-4 iodobenzene 
• 80581-21-1 [(2R,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-methanol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 35756-26-4 2,3-dihydro-5-phenyl-1,4-dithiin 
• 267665-92-9 (1R,5'R)-1-p-nitrobenzoic acid-1-(2',2'-dimethyl-[1',3']dioxolan-4'-yl)-3-phenyl-prop-2-ynyl 
• 208114-17-4 (1S,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4-yl)-3-phenyl-prop-2-yn-ol 
• 4688-38-4 (2R,3S)-1,2-O-isopropylidene-4-pentyne-1,2,3-triol 
• 208114-18-5 (1R,5'R)-1-(2',2'-dimethyl-[1',3']dioxolan-4-yl)-3-phenyl-prop-2-yn-ol 

Downstream Products

• 208048-45-7 trans-(1R,5'R)-1-diazoacetic acid 1-(2',2'-dimethyl-[1',3']dioxolane-4'-yl)-3-phenyl-prop-2-enyl ester 

Relevant academic research and scientific papers

Applications of intramolecular cyclopropanations of chiral secondary allylic diazoacetates

The diastereomeric secondary allylic diazoacetates 6a,b and 8a,b, which were readily prepared from the common intermediate 4, were cyclized in the presence of the achiral catalyst Cu(TBS)2 to furnish mixtures of the adducts 9a,b/10a,b and 12a,b/13a,b, respectively; in these cyclizations, the diastereoselectivity of the reaction was substrate controlled. When 6a,b and 8a,b were cyclized in the presence of the chiral catalysts Rh2[(5S)-MEPY]4 or Rh2[(5A)-MEPY]4, the substrate-based selectivity could be reversed if the chirality of the substrate and catalyst were matched. The advantages associated with the use of chiral catalysts to effect the diastereoselective cyclization of chiral allylic diazoacetates were demonstrated by the synthesis of 25, which comprises the cyclopropane subunit found in the diterpene ingol B (14).

Diastereodifferentiation in intramolecular cyclopropanations of chiral secondary allylic diazoacetates

Intramolecular cyclopropanations of diastereomeric, secondary allylic diazoacetates were carried out in the presence of an achiral copper catalyst, Cu(TBS)2, and the chiral rhodium catalysts Rh2[5(S)-MEPY]4 and Rh2[5(R)- MEPY]4 to give diastereomeric cyclopropyl lactones in ratios that varied with catalyst and stereochemistry of the starting material.

Asymmetric induction in the coupling of 5,6-dihydro-1,4-dithiins with chiral aldehydes. A new synthetic approach to polyhydroxylated compounds

A new strategy is designed to synthesize polyhydroxyl compounds (and/or carbohydrates) by coupling of 5,6-dihydro-1,4-dithiins - carrying a vinylic hydrogen atom - with chiral aldehydes and, in sequence, stereoselective removal of the dithiodimethylene di

An expeditious approach for the synthesis of optically active allyl alcohols

Aldehyde tosylhydrazones having an adjacent O-isopropylidene group undergo a condensation-fragmentation process in the presence of alkyl magnesium and alkyllithium reagents to yield chiral allyl alcohols.

Alkylative Elimination of α,β-Epoxy Tosylhydrazones

Optically pure allyl alcohols have been prepared from tosylhydrazones derived from chiral epoxy aldehydes by alkylative elimination utilizing alkyl magnesium reagents.