Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C 2-1,1′-Bitetrahydroisoquinolines

Khong Duc Thinh; Zaher M.A. Judeh

doi:10.1055/s-0034-1378892

Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C ₂-1,1′-Bitetrahydroisoquinolines

Khong Duc Thinh, Zaher M.A. Judeh^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C₂ -1,1′-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono- and dialdehydes using inexpensive sulfuric acid as the catalyst.

Original language	English
Article number	ss-2014-n0224-op
Pages (from-to)	2780-2788
Number of pages	9
Journal	Synthesis
Volume	46
Issue number	20
DOIs	https://doi.org/10.1055/s-0034-1378892
Publication status	Published - Oct 16 2014
Externally published	Yes

Bibliographical note

Publisher Copyright:
© Georg Thieme Verlag Stuttgart. New York.

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

C -symmetric chiral ligands
chiral bitetrahydroisoquinolines
diastereoselective Pictet-SpenglerAreaction
isoquinoline
stereoselective synthesis

Access to Document

10.1055/s-0034-1378892

Cite this

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title = "Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C 2-1,1′-Bitetrahydroisoquinolines",

abstract = "An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C2 -1,1′-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono- and dialdehydes using inexpensive sulfuric acid as the catalyst.",

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T1 - Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C 2-1,1′-Bitetrahydroisoquinolines

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AU - Judeh, Zaher M.A.

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart. New York.

PY - 2014/10/16

Y1 - 2014/10/16

N2 - An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C2 -1,1′-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono- and dialdehydes using inexpensive sulfuric acid as the catalyst.

AB - An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C2 -1,1′-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono- and dialdehydes using inexpensive sulfuric acid as the catalyst.

KW - C -symmetric chiral ligands

KW - chiral bitetrahydroisoquinolines

KW - diastereoselective Pictet-SpenglerAreaction

KW - isoquinoline

KW - stereoselective synthesis

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