Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C2-1,1′-Bitetrahydroisoquinolines

Khong Duc Thinh; Zaher M. A. Judeh

doi:10.1055/s-0034-1378892

Synthesis, Table of Contents

Synthesis 2014; 46(20): 2780-2788
DOI: 10.1055/s-0034-1378892

paper

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

Khong Duc Thinh

School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2 B1-14, 637459, Singapore Fax: +65-67947553 Email: zaher@ntu.edu.sg

,

Zaher M. A. Judeh*

School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2 B1-14, 637459, Singapore Fax: +65-67947553 Email: zaher@ntu.edu.sg

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Abstract

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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.

Key words

stereoselective synthesis - chiral bitetrahydroisoquinolines - C ₂-symmetric chiral ligands - diastereoselective Pictet–Spengler reaction - isoquinoline

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References

References

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Supplementary Material

Supporting Information

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

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