PMID- 32270678
OWN - NLM
STAT- MEDLINE
DCOM- 20220530
LR  - 20220530
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 85
IP  - 9
DP  - 2020 May 1
TI  - Construction of 1,3-Oxazolidines through a Three-Component [3+2] Cycloaddition of 
      Tetrahydroisoquinolines, Aldehydes, and Ethyl Ketomalonate.
PG  - 6216-6224
LID - 10.1021/acs.joc.0c00616 [doi]
AB  - A chemoselective and diastereoselective synthesis of fused oxazolidines was 
      achieved by a three-component cascade reaction of tetrahydroisoquinolines 
      (THIQs), alpha,beta-unsaturated aldehydes, and diethyl 2-oxomalonate. Probably due to 
      the reactivity difference between the aldehyde and the ketone, the reaction 
      proceeded through the condensation of THIQs with alpha,beta-unsaturated aldehydes and 
      1,3-dipolar cycloaddition of the generated azomethine ylide intermediate with 
      2-oxomalonate. The key features are easily available starting materials, mild 
      reaction conditions, broad substrate scope, and high chemo- and 
      diastereoselectivity.
FAU - Wu, Xiang
AU  - Wu X
AUID- ORCID: 0000-0001-5428-9063
AD  - Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction 
      Engineering, School of Chemistry and Chemical Engineering, Hefei University of 
      Technology, Hefei 230009, China.
FAU - Zhu, Zheng-Hao
AU  - Zhu ZH
AD  - Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction 
      Engineering, School of Chemistry and Chemical Engineering, Hefei University of 
      Technology, Hefei 230009, China.
FAU - He, Hao
AU  - He H
AD  - Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction 
      Engineering, School of Chemistry and Chemical Engineering, Hefei University of 
      Technology, Hefei 230009, China.
FAU - Ren, Lei
AU  - Ren L
AD  - College of Materials and Chemical Engineering, Bengbu University, Bengbu 233030, 
      China.
FAU - Zhu, Cheng-Feng
AU  - Zhu CF
AUID- ORCID: 0000-0002-9676-6750
AD  - Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction 
      Engineering, School of Chemistry and Chemical Engineering, Hefei University of 
      Technology, Hefei 230009, China.
FAU - Li, You-Gui
AU  - Li YG
AD  - Anhui Province Key Laboratory of Advanced Catalytic Materials and Reaction 
      Engineering, School of Chemistry and Chemical Engineering, Hefei University of 
      Technology, Hefei 230009, China.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20200415
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
RN  - 0 (Aldehydes)
RN  - 0 (Amines)
RN  - 0 (Malonates)
RN  - 0 (Oxazoles)
RN  - 0 (Tetrahydroisoquinolines)
RN  - 13F52UF6MR (oxazolidine)
RN  - 62R514HE48 (mesoxalic acid)
SB  - IM
MH  - *Aldehydes
MH  - Amines
MH  - Cyclization
MH  - Cycloaddition Reaction
MH  - Malonates
MH  - Oxazoles
MH  - Stereoisomerism
MH  - *Tetrahydroisoquinolines
EDAT- 2020/04/10 06:00
MHDA- 2022/05/31 06:00
CRDT- 2020/04/10 06:00
PHST- 2020/04/10 06:00 [pubmed]
PHST- 2022/05/31 06:00 [medline]
PHST- 2020/04/10 06:00 [entrez]
AID - 10.1021/acs.joc.0c00616 [doi]
PST - ppublish
SO  - J Org Chem. 2020 May 1;85(9):6216-6224. doi: 10.1021/acs.joc.0c00616. Epub 2020 
      Apr 15.