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

Wing Hong 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

Wing Hong CHAN^*, Albert W M LEE, Lasheng Jiang

^*Corresponding author for this work

Department of Chemistry

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

26 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

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(94)02323-4

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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 = "CHAN, {Wing Hong} and LEE, {Albert W M} and Lasheng Jiang",

year = "1995",

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day = "30",

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

language = "English",

volume = "36",

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journal = "Tetrahedron Letters",

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T1 - Chiral acetylenic sulfoxides in organic synthesis

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

AU - CHAN, Wing Hong

AU - LEE, Albert W M

AU - Jiang, Lasheng

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.

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

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

M3 - Article

AN - SCOPUS:0028819486

VL - 36

SP - 715

EP - 718

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 5

ER -

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

Abstract

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