PMID- 24237286
OWN - NLM
STAT- MEDLINE
DCOM- 20140502
LR  - 20140204
IS  - 1523-7052 (Electronic)
IS  - 1523-7052 (Linking)
VI  - 15
IP  - 23
DP  - 2013 Dec 6
TI  - CuI-catalyzed C1-alkynylation of tetrahydroisoquinolines (THIQs) by A3 reaction 
      with tunable iminium ions.
PG  - 5928-31
LID - 10.1021/ol402517e [doi]
AB  - A CuI-catalyzed A(3) (amines, aldehydes and alkynes) reaction of 
      tetrahydroisoquinolines (THIQs), aldehydes, and alkynes to give C1-alkynylated 
      THIQ products (endo-yne-THIQs) was developed. This redox neutral C1-alkynylation 
      of THIQs, which was conducted under mild conditions, has a broad scope for the 
      used aldehydes and alkynes. It was proposed that the A(3) reaction first 
      generates in situ exo-iminium ions, which then isomerize to endo-iminium ions and 
      react with copper acetylides to give the endo alkynylated THIQs (endo-yne-THIQs).
FAU - Zheng, Qin-Heng
AU  - Zheng QH
AD  - Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of 
      Bioorganic Chemistry and Molecular Engineering, College of Chemistry, Peking 
      University , Beijing, 100871, China.
FAU - Meng, Wei
AU  - Meng W
FAU - Jiang, Guo-Jie
AU  - Jiang GJ
FAU - Yu, Zhi-Xiang
AU  - Yu ZX
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20131115
PL  - United States
TA  - Org Lett
JT  - Organic letters
JID - 100890393
RN  - 0 (Aldehydes)
RN  - 0 (Alkynes)
RN  - 0 (Amines)
RN  - 0 (Iodides)
RN  - 0 (Tetrahydroisoquinolines)
RN  - 789U1901C5 (Copper)
RN  - 7DE9CA6IL2 (cuprous iodide)
SB  - IM
MH  - Aldehydes/*chemistry
MH  - Alkynes/*chemistry
MH  - Amines/*chemistry
MH  - Catalysis
MH  - Copper/*chemistry
MH  - Iodides/*chemistry
MH  - Molecular Structure
MH  - Oxidation-Reduction
MH  - Stereoisomerism
MH  - Tetrahydroisoquinolines/*chemistry
EDAT- 2013/11/19 06:00
MHDA- 2014/05/03 06:00
CRDT- 2013/11/19 06:00
PHST- 2013/11/19 06:00 [entrez]
PHST- 2013/11/19 06:00 [pubmed]
PHST- 2014/05/03 06:00 [medline]
AID - 10.1021/ol402517e [doi]
PST - ppublish
SO  - Org Lett. 2013 Dec 6;15(23):5928-31. doi: 10.1021/ol402517e. Epub 2013 Nov 15.