99439-87-9

Upstream product

• 81028-03-7 (Z)-4-benzyloxy-but-2-en-1-ol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 174676-86-9 (S)-N-<4-benzyloxy-2(Z)-buten-1-yl>-N-<1-phenyleth-1-yl>amine 
• 174676-90-5 (S)-N-<4-benzyloxy-2(Z)-buten-1-yl>-N-(1-phenyleth-1-yl)-3-oxobutanamide 
• 177186-31-1 (Z)-(S)-6-Benzyloxy-2-((S)-1-phenyl-ethylamino)-hex-4-enoic acid amide 
• 176966-50-0 (Z)-(R)-6-Benzyloxy-2-((S)-1-phenyl-ethylamino)-hex-4-enoic acid amide 
• 790251-81-9 4-[N-benzyl-N-(4-benzyloxy)but-2-enylamino]-1-diazo-2-butanone 
• 936845-06-6 3-(3-benzyloxymethyl-oxiranylmethyl)-6-methyl-4-(1-phenyl-ethyl)-morpholine-2,5-dione 
• 936845-06-6 3-(3-benzyloxymethyl-oxiranylmethyl)-6-methyl-4-(1-phenyl-ethyl)-morpholine-2,5-dione 
• 936845-16-8 3-(3-benzyloxymethyl-oxiranylmethyl)-6-methyl-4-(1-phenyl-ethyl)-morpholine-2,5-dione 
• 936845-16-8 3-(3-benzyloxymethyl-oxiranylmethyl)-6-methyl-4-(1-phenyl-ethyl)-morpholine-2,5-dione 
• 936845-20-4 (3S,6R,2'R,3'S)-3-(4'-benzyloxy-2',3'-dihydroxybutyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione 
• 936845-18-0 (3S,6R,2'R,3'R)-3-(4'-benzyloxy-2',3'-dihydroxybutyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione 
• 936845-19-1 (3S,6R,2'S,3'R)-3-(4'-benzyloxy-2',3'-dihydroxybutyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione 
• 936845-08-8 (3R,6S,2'R,3'R)-3-(4'-benzyloxy-2',3'-dihydroxybutyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione 
• 936845-07-7 (3R,6S,2'S,3'S)-3-(4'-benzyloxy-2',3'-dihydroxybutyl)-6-methyl-4-[(S)-phenethyl]-morpholine-2,5-dione 

Relevant academic research and scientific papers

Ruthenium porphyrin catalyzed tandem sulfonium/ammonium ylide formation and [2,3]-sigmatropic rearrangement. A concise synthesis of (±)-platynecine

meso-Tetrakis(p-tolyl)porphyrinatoruthenium(II) carbonyl, [Ru II(TTP)(CO)], can effect intermolecular sulfonium and ammonium ylide formation by catalytic decomposition of diazo compounds such as ethyl diazoacetate (EDA) in the presence of allyl sulfides and amines. Exclusive formation of [2,3]-sigmatropic rearrangement products (70-80% yields) was observed without [1,2]-rearrangement products being detected. The Ru-catalyzed reaction of EDA with disubstituted allyl sulfides such as crotyl sulfide produced an equimolar mixture of anti- and syn-2-(ethylthio)-3-methyl-4- pentenoic acid ethyl ester. The analogous "EDA + N,N- dimethylcrotylamine" reaction afforded a mixture of anti- and syn-2-(N,N-dimethylamino)-3-methyl-4-pentenoic acid ethyl esters with a diastereoselectivity of 3:1. The observed catalytic activity of [Ru II(TTP)(CO)] for the ylide [2,3]-sigmatropic rearrangement is comparable to the reported examples involving [Rh2(CH 3CO2)4] and [Cu(acac)2] as catalyst. Similarly, cyclic sulfonium and ammonium ylides can be produced by intramolecular reaction of a diazo group tethered to allyl sulfides and amines under the [RuII-(TTP)(CO)]-catalyzed reaction conditions. The subsequent [2,3]-sigmatropic rearrangement of the cyclic ylides furnished 2-allyl-substituted sulfur and nitrogen heterocycles in good yields (>90%). By employing [RuII(TTP)(CO)] as catalyst, the cyclic ammonium ylide [2,3]-sigmatropic rearrangement reaction was successfully applied for the total synthesis of (±)-platynecine starting from cis-2-butenediol.

Enantioselective Preparation of 3-Substituted-4-pentenoic Acids via the Claisen Rearrangement

Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described.The starting materials, allylic alkylating agant 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94percent diastereomeric excess.The overall chemical yields for 2 -> 5 range from 51 to 78percent.The aza-Claisen rearrangement (4 -> 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity.Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.