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A convenient synthesis of 2-methoxy-1-naphthyl sulfoxides in high enantiomeric purity. A new asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines

Journal Article


Abstract


  • The synthesis of diastereomerically pure (-)-(S) menthyl 2-methoxy-1-naphthalenesulfinate (5) is reported. The reaction of (5) with methylmagnesium iodode or benzylmagnesium chloride gives (+)-(R) methyl and (+)-(R) benzyl 2-methoxy-1-naphthyl sulfoxide, (7) and (8) respectively, in high enantiomeric purity (98% ee). Lithiated (8) undergoes addition to 6,7-dimethoxy-3,4-dihydroisoquinoline N-oxide (2) to give a 1-benzyl-1,2,3,4-tetrahydroisoquinoline derivative (9) with high product diastereoselection (d. r. 96 : 4). The stereochemistry of (9) was determined by a single crystal X-ray structure determination. © 1994.

Publication Date


  • 1994

Citation


  • Pyne, S. G., Hajipour, A. R., & Prabakaran, K. (1994). A convenient synthesis of 2-methoxy-1-naphthyl sulfoxides in high enantiomeric purity. A new asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines. Tetrahedron Letters, 35(4), 645-648. doi:10.1016/S0040-4039(00)75860-6

Scopus Eid


  • 2-s2.0-0028273289

Web Of Science Accession Number


Start Page


  • 645

End Page


  • 648

Volume


  • 35

Issue


  • 4

Abstract


  • The synthesis of diastereomerically pure (-)-(S) menthyl 2-methoxy-1-naphthalenesulfinate (5) is reported. The reaction of (5) with methylmagnesium iodode or benzylmagnesium chloride gives (+)-(R) methyl and (+)-(R) benzyl 2-methoxy-1-naphthyl sulfoxide, (7) and (8) respectively, in high enantiomeric purity (98% ee). Lithiated (8) undergoes addition to 6,7-dimethoxy-3,4-dihydroisoquinoline N-oxide (2) to give a 1-benzyl-1,2,3,4-tetrahydroisoquinoline derivative (9) with high product diastereoselection (d. r. 96 : 4). The stereochemistry of (9) was determined by a single crystal X-ray structure determination. © 1994.

Publication Date


  • 1994

Citation


  • Pyne, S. G., Hajipour, A. R., & Prabakaran, K. (1994). A convenient synthesis of 2-methoxy-1-naphthyl sulfoxides in high enantiomeric purity. A new asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines. Tetrahedron Letters, 35(4), 645-648. doi:10.1016/S0040-4039(00)75860-6

Scopus Eid


  • 2-s2.0-0028273289

Web Of Science Accession Number


Start Page


  • 645

End Page


  • 648

Volume


  • 35

Issue


  • 4