Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine

Winghong Chan; Albert W.M. Lee; Lasheng Jiang

doi:10.1016/0040-4039(94)02323-4

Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine

Winghong Chan^*
, Albert W.M. Lee
, Lasheng Jiang

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

27 Citations (Scopus)

Abstract

Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been synthesized.

Original language	English
Pages (from-to)	715-718
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	5
DOIs	https://doi.org/10.1016/0040-4039(94)02323-4
Publication status	Published - 30 Jan 1995

Access to Document

10.1016/0040-4039(94)02323-4

Cite this

@article{b190f8ee4de04be1878e1aee1dd604d4,

title = "Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine",

abstract = "Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been synthesized.",

author = "Winghong Chan and Lee, \{Albert W.M.\} and Lasheng Jiang",

note = "Financial support from the Research Grant Council of the UPGC is gratefully acknowledged. The high field NMR facility is supported by funds provided by the UPGC and the Croucher Foundation. ",

year = "1995",

month = jan,

day = "30",

doi = "10.1016/0040-4039(94)02323-4",

language = "English",

volume = "36",

pages = "715--718",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "5",

}

TY - JOUR

T1 - Chiral acetylenic sulfoxides in organic synthesis

T2 - Secondary amine cyclization and total synthesis of (S)-(-)-carnegine

AU - Chan, Winghong

AU - Lee, Albert W.M.

AU - Jiang, Lasheng

N1 - Financial support from the Research Grant Council of the UPGC is gratefully acknowledged. The high field NMR facility is supported by funds provided by the UPGC and the Croucher Foundation.

PY - 1995/1/30

Y1 - 1995/1/30

N2 - Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been synthesized.

AB - Michael addition of secondary amines 1b-1g onto chiral acetylenic sulfoxides 2 followed by acid induced cyclization afforded structures of tetrahydroisoquinoline skeleton in high to moderate diastereoselectivity. Optical pure (S)-(-)-carnegine has been synthesized.

UR - https://www.scopus.com/pages/publications/0028819486

U2 - 10.1016/0040-4039(94)02323-4

DO - 10.1016/0040-4039(94)02323-4

M3 - Journal article

AN - SCOPUS:0028819486

SN - 0040-4039

VL - 36

SP - 715

EP - 718

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Chiral acetylenic sulfoxides in organic synthesis: Secondary amine cyclization and total synthesis of (S)-(-)-carnegine

Abstract

Access to Document

Other files and links

Fingerprint

Cite this