PMID- 32850649
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20200928
IS  - 2296-2646 (Print)
IS  - 2296-2646 (Electronic)
IS  - 2296-2646 (Linking)
VI  - 8
DP  - 2020
TI  - Direct and Efficient C(sp(3))-H Functionalization of N-Acyl/Sulfonyl 
      Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 
      2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation.
PG  - 629
LID - 10.3389/fchem.2020.00629 [doi]
LID - 629
AB  - A highly efficient metal-free oxidative direct C(sp(3))-H functionalization of 
      N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) with a wide range of 
      electron-rich nucleophiles was accomplished under mild conditions through 
      oxidation with DDQ and subsequent trapping of the resulting reactive and stable 
      N-acyl/sulfonyl iminium ions. The synthetic utility of this method was 
      illustrated by a concise and efficient total synthesis of 
      (+/-)-benzo[a]quinolizidine (10) in 3 steps from the known N-Cbz 1,2,3,4-THIQ 4b.
CI  - Copyright (c) 2020 Yu, Kim, Baek and Lee.
FAU - Yu, Heesun
AU  - Yu H
AD  - Research Institute of Pharmaceutical Science and Technology (RIPST), College of 
      Pharmacy, Ajou University, Suwon, South Korea.
FAU - Kim, Hyoungsu
AU  - Kim H
AD  - Research Institute of Pharmaceutical Science and Technology (RIPST), College of 
      Pharmacy, Ajou University, Suwon, South Korea.
FAU - Baek, Seung-Hoon
AU  - Baek SH
AD  - Research Institute of Pharmaceutical Science and Technology (RIPST), College of 
      Pharmacy, Ajou University, Suwon, South Korea.
FAU - Lee, Dongjoo
AU  - Lee D
AD  - Research Institute of Pharmaceutical Science and Technology (RIPST), College of 
      Pharmacy, Ajou University, Suwon, South Korea.
LA  - eng
PT  - Journal Article
DEP - 20200729
PL  - Switzerland
TA  - Front Chem
JT  - Frontiers in chemistry
JID - 101627988
PMC - PMC7403605
OTO - NOTNLM
OT  - DDQ
OT  - electron-rich
OT  - natural products
OT  - oxidation
OT  - tetrahydroisoquinoline
EDAT- 2020/08/28 06:00
MHDA- 2020/08/28 06:01
PMCR- 2020/01/01
CRDT- 2020/08/28 06:00
PHST- 2020/04/04 00:00 [received]
PHST- 2020/06/17 00:00 [accepted]
PHST- 2020/08/28 06:00 [entrez]
PHST- 2020/08/28 06:00 [pubmed]
PHST- 2020/08/28 06:01 [medline]
PHST- 2020/01/01 00:00 [pmc-release]
AID - 10.3389/fchem.2020.00629 [doi]
PST - epublish
SO  - Front Chem. 2020 Jul 29;8:629. doi: 10.3389/fchem.2020.00629. eCollection 2020.