The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

Varinder K. Aggarwal; Nekane Barbero; Eoghan M. McGarrigle; Greg Mickle; Raquel Navas-Garcia; Jose Ramon Suarez-Alvarez; Matthew G. Unthank; Muhammad Yar

doi:10.1016/j.tetlet.2009.03.020

The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

Varinder K. Aggarwal^*
, Nekane Barbero
, Eoghan M. McGarrigle
, Greg Mickle
, Raquel Navas-Garcia
, Jose Ramon Suarez-Alvarez
, Matthew G. Unthank
, Muhammad Yar

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

49 Citations (Scopus)

Abstract

Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3482-3484
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.020
Publication status	Published - 1 Jul 2009

Research Groups and Themes

Organic & Biological

Keywords

Ellman's auxiliary
tert-Butylsulfinamide
Sulfinimines
Deprotection
Cleavage
Dynamic kinetic resolution
DYNAMIC KINETIC RESOLUTION
ASYMMETRIC-SYNTHESIS
SULFINYL CHLORIDES
BUTANESULFINYL IMINES
BIS-SULFOXIDES
AMINES
DAG
SULFINIMINES
COMBINATIONS
SULFINAMIDES

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@article{ab55793109144569803268ee73457a7e,

title = "The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2",

abstract = "Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "Ellman's auxiliary, tert-Butylsulfinamide, Sulfinimines, Deprotection, Cleavage, Dynamic kinetic resolution, DYNAMIC KINETIC RESOLUTION, ASYMMETRIC-SYNTHESIS, SULFINYL CHLORIDES, BUTANESULFINYL IMINES, BIS-SULFOXIDES, AMINES, DAG, SULFINIMINES, COMBINATIONS, SULFINAMIDES",

author = "Aggarwal, \{Varinder K.\} and Nekane Barbero and McGarrigle, \{Eoghan M.\} and Greg Mickle and Raquel Navas-Garcia and Suarez-Alvarez, \{Jose Ramon\} and Unthank, \{Matthew G.\} and Muhammad Yar",

year = "2009",

month = jul,

day = "1",

doi = "10.1016/j.tetlet.2009.03.020",

language = "English",

volume = "50",

pages = "3482--3484",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "26",

}

TY - JOUR

T1 - The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

AU - Aggarwal, Varinder K.

AU - Barbero, Nekane

AU - McGarrigle, Eoghan M.

AU - Mickle, Greg

AU - Navas-Garcia, Raquel

AU - Suarez-Alvarez, Jose Ramon

AU - Unthank, Matthew G.

AU - Yar, Muhammad

PY - 2009/7/1

Y1 - 2009/7/1

N2 - Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.

AB - Ellman's chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH2. (C) 2009 Elsevier Ltd. All rights reserved.

KW - Ellman's auxiliary

KW - tert-Butylsulfinamide

KW - Sulfinimines

KW - Deprotection

KW - Cleavage

KW - Dynamic kinetic resolution

KW - DYNAMIC KINETIC RESOLUTION

KW - ASYMMETRIC-SYNTHESIS

KW - SULFINYL CHLORIDES

KW - BUTANESULFINYL IMINES

KW - BIS-SULFOXIDES

KW - AMINES

KW - DAG

KW - SULFINIMINES

KW - COMBINATIONS

KW - SULFINAMIDES

U2 - 10.1016/j.tetlet.2009.03.020

DO - 10.1016/j.tetlet.2009.03.020

M3 - Article (Academic Journal)

SN - 0040-4039

VL - 50

SP - 3482

EP - 3484

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage-a method for recycling t-BuSONH2

Abstract

Research Groups and Themes

Keywords

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