220765-22-0

Upstream product

• 253676-12-9 (3S,4S)-5-Methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-1-yn-3-ol 
• 253675-93-3 Methyl (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate 
• 220765-48-0 (2S,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine 
• 220765-18-4 (2R,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine 
• 293299-48-6 (4S,2E)-2-bromo-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-yl methyl-sulfonate 
• 220324-12-9 (4S,2Z)-2-Bromo-O-methylsulfonyl-5-methyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 
• 917-54-4 methyllithium 

Downstream Products

• 627079-71-4 N-(2-methylprop-2-enyl)-N-[(1S)-1-isopropylbuta-2,3-dienyl]-2,4,6-trimethylphenylsulfonamide 
• 597540-65-3 N-allyl-N-[(1S)-1-isopropylbuta-2,3-dienyl]-2,4,6-trimethylphenylsulfonamide 
• 597540-82-4 N-[(1S)-1-isopropylbuta-2,3-dienyl]-2,4,6-trimethyl-N-[(E)-3-phenyl-2-propenyl]phenylsulfonamide 
• 862265-63-2 N-[(1S)-1-isopropylbuta-2,3-dienyl]-2,4,6-trimethyl-N-[(Z)-3-phenyl-2-propenyl]phenylsulfonamide 
• 1026532-11-5 C₂₃H₃₅NO₄S 
• 867297-08-3 N-[(1S)-1-isopropylbuta-2,3-dienyl]-N-[(E)-3-(4-methoxyphenyl)prop-2-enyl]-2,4,6-trimethylphenylsulfonamide 

Relevant academic research and scientific papers

Synthesis of chiral amino allenes via an organocyanocuprate-mediated ring-opening reaction of enantiopure ethynylaziridines

Amino allenes have been synthesized from 2-ethynylaziridines via organocopper-mediated reactions. Whereas treatment of enantiomerically pure (2R,3S)-2,3-trans-3-alkyl-3-ethynylaziridines with RCu(CN)M (M = Li or MgX) yield exclusively (S,S)-allenylamines

Synthesis of allenes from allylic alcohol derivatives bearing a bromine atom using a palladium(0)/diethylzinc system

A general and efficient synthesis of allenes using a palladium(0)/diethylzinc system is described. Treatment of mesylates or trichloroacetates of (E)- or (Z)-2-bromoalk-2-en-1-ols with diethylzinc in the presence of a catalytic amount of palladium(0) affords allenes bearing an aminoalkyl, alkyl, or aryl substituent(s) in good to high yields. No transfer of chirality from the stereogenic center carrying the mesyloxy group to the allene was observed.

2-Ethynylaziridines as chiral carbon nucleophiles: Stereoselective synthesis of 1,3-amino alcohols with three stereocenters via allenylindium reagents bearing a protected amino group

Allenylindium reagents bearing a protected amino group were effectively prepared from N-protected 3-alkyl-2-ethynylaziridines by treatment with InI in the presence of Pd(PPh3)4 and H2O. Stereo-selective addition of the allenylindium to aliphatic or aromatic aldehydes affords 1,3-amino alcohols bearing three contiguous chiral centers: while 2,3-trans-2-ethynylaziridines yield syn,syn-2-ethynyl-1,3-amino alcohols predominantly, 2,3-cis-aziridines give anti,syn isomers selectively. Synthesis of highly substituted ethynylazetidines is also described.

Novel synthesis of chiral terminal allenes via palladium(o)catalyzed reduction of mesylates of 2-bromoalk-2-en-1-ols bearing a protected amino group, using diethylzinc

A novel palladium(0)-catalyzed synthetic route to a series of chiral terminal allenes bearing an N-protected amino alkyl group has been developed. The palladium(0)-catalyzed reaction of mesylates of 2-bromoalk-2-en-1-ols bearing an amino functionality, with diethylzinc affords the corresponding terminal allenes in good yields. Both (E)- and (Z)-bromomesylates can equally be used for the present reaction, yielding the desired allenes in comparable yields. (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of chiral amino allenes by organocopper- mediated anti-S(N)2'-substitution reaction of chiral ethynylaziridines

Chiral N-protected amino allenes have been synthesized from 3-alkyl-2- ethynylaziridines via organocopper-mediated reactions. Treatment of enantiomerically pure (2R,3S)-2,3-trans-3-alkyl-2-ethynylaziridines with RCu(CN)M (M=Li or MgX) in THF at -78°C affords exclusively the expected (S,S)-amino allenes in high yields in a regio- and stereoselective manner. On the other hand, (2S,3S)-2,3,cis-3-alkyl-2-ethynylaziridines give stereoisomeric (S,R)-amino allenes in comparable high yields. (C) 2000 Elsevier Science Ltd.