Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols

Andrés Villalpando; Mirza A. Saputra; Thomas H. Tugwell; Rendy Kartika

doi:10.1039/c5cc06365e

Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols

Andrés Villalpando, Mirza A. Saputra, Thomas H. Tugwell, Rendy Kartika

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

13 Citations (Scopus)

Abstract

We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.

Original language	English
Pages (from-to)	15075-15078
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	81
DOIs	https://doi.org/10.1039/c5cc06365e
Publication status	Published - 14 Aug 2015

Access to Document

10.1039/c5cc06365e

Cite this

@article{3aa7470e0bf848c6a2da7bb8f9651974,

title = "Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols",

abstract = "We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.",

author = "Andr{\'e}s Villalpando and Saputra, {Mirza A.} and Tugwell, {Thomas H.} and Rendy Kartika",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2015",

month = aug,

day = "14",

doi = "10.1039/c5cc06365e",

language = "English",

volume = "51",

pages = "15075--15078",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "81",

}

TY - JOUR

T1 - Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols

AU - Villalpando, Andrés

AU - Saputra, Mirza A.

AU - Tugwell, Thomas H.

AU - Kartika, Rendy

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2015/8/14

Y1 - 2015/8/14

N2 - We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.

AB - We describe a strategy to chlorinate stereocomplementary acyclic aliphatic 1,3-diols using a mixture of triphosgene and pyridine. While 1,3-anti diols readily led to 1,3-anti dichlorides, 1,3-syn diols must be converted to 1,3-syn diol monosilylethers to access the corresponding 1,3-syn dichlorides. These dichlorination protocols were operationally simple, very mild, and readily tolerated by advanced synthetic intermediates.

UR - http://www.scopus.com/inward/record.url?scp=84942934924&partnerID=8YFLogxK

U2 - 10.1039/c5cc06365e

DO - 10.1039/c5cc06365e

M3 - Article

C2 - 26323232

AN - SCOPUS:84942934924

SN - 1359-7345

VL - 51

SP - 15075

EP - 15078

JO - Chemical Communications

JF - Chemical Communications

IS - 81

ER -

Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols

Abstract

Access to Document

Fingerprint

Cite this