293299-54-4

Upstream product

• 220324-15-2 (4S,2Z)-2-Bromo-O-methylsulfonyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol 
• 293299-50-0 (4S,2E)-2-bromo-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-yl methyl-sulfonate 
• 1026635-31-3 (4S,2E)-2-bromo-4-[N-(tert-butoxycarbonyl)amino]-5-phenylpent-2-en-1-ol 
• 253676-00-5 Methyl (4S,2E)-2-bromo-4-[N-(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 

Downstream Products

• 597540-66-4 N-allyl-N-[(1S)-1-benzylbuta-2,3-dienyl]-2,4,6-trimethylphenylsulfonamide 

Relevant academic research and scientific papers

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.

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.