Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative

Jongho Jeon; Moonyong Shin; Jae Won Yoo; Joon Seok Oh; Jae Gwang Bae; Seung Hwan Jung; Young Gyu Kim

doi:10.1016/j.tetlet.2006.12.084

Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative

Jongho Jeon, Moonyong Shin, Jae Won Yoo, Joon Seok Oh, Jae Gwang Bae, Seung Hwan Jung, Young Gyu Kim

Department of Applied Chemistry

Seoul National University

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

26 Scopus citations

Abstract

Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO₄-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) was shown in CH₂Cl₂. An efficient stereoselective synthesis of a tetraacetyl derivative of d-ribo-phytosphingosine was reported using the N,N-diBoc-controlled dihydroxylation from Garner's aldehyde.

Original language	English
Pages (from-to)	1105-1108
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2006.12.084
State	Published - 12 Feb 2007

Access to Document

10.1016/j.tetlet.2006.12.084

Cite this

@article{4ca684a30a1248d8a10f38ccf6f68f3a,

title = "Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative",

abstract = "Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO4-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) was shown in CH2Cl2. An efficient stereoselective synthesis of a tetraacetyl derivative of d-ribo-phytosphingosine was reported using the N,N-diBoc-controlled dihydroxylation from Garner's aldehyde.",

author = "Jongho Jeon and Moonyong Shin and Yoo, {Jae Won} and Oh, {Joon Seok} and Bae, {Jae Gwang} and Jung, {Seung Hwan} and Kim, {Young Gyu}",

year = "2007",

month = feb,

day = "12",

doi = "10.1016/j.tetlet.2006.12.084",

language = "English",

volume = "48",

pages = "1105--1108",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "7",

}

TY - JOUR

T1 - Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines

T2 - stereoselective synthesis of a d-ribo-phytosphingosine derivative

AU - Jeon, Jongho

AU - Shin, Moonyong

AU - Yoo, Jae Won

AU - Oh, Joon Seok

AU - Bae, Jae Gwang

AU - Jung, Seung Hwan

AU - Kim, Young Gyu

PY - 2007/2/12

Y1 - 2007/2/12

N2 - Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO4-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) was shown in CH2Cl2. An efficient stereoselective synthesis of a tetraacetyl derivative of d-ribo-phytosphingosine was reported using the N,N-diBoc-controlled dihydroxylation from Garner's aldehyde.

AB - Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO4-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) was shown in CH2Cl2. An efficient stereoselective synthesis of a tetraacetyl derivative of d-ribo-phytosphingosine was reported using the N,N-diBoc-controlled dihydroxylation from Garner's aldehyde.

UR - http://www.scopus.com/inward/record.url?scp=33846213597&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2006.12.084

DO - 10.1016/j.tetlet.2006.12.084

M3 - Article

AN - SCOPUS:33846213597

SN - 0040-4039

VL - 48

SP - 1105

EP - 1108

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative

Abstract

Access to Document

Other files and links

Fingerprint

Cite this