Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives

Seijiro Matsubara, Yuri Kasuga, Takuya Yasui, Masahito Yoshioka, Bohari Mohd. Yamin, Kiitiro Utimoto, Koichiro Oshima

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Both enantiomers of 3-hydroxyalkanoates and -alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and α-bromoamide is also discussed.

Original languageEnglish
Pages (from-to)38-40
Number of pages3
JournalChirality
Volume15
Issue number1
DOIs
Publication statusPublished - 2003

Fingerprint

Samarium
Enantiomers
Iodides
Ketones
Derivatives
oxathiane

Keywords

  • Aldol
  • Diastereoselective
  • Enolate
  • Samarium

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Matsubara, S., Kasuga, Y., Yasui, T., Yoshioka, M., Mohd. Yamin, B., Utimoto, K., & Oshima, K. (2003). Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives. Chirality, 15(1), 38-40. https://doi.org/10.1002/chir.10147

Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives. / Matsubara, Seijiro; Kasuga, Yuri; Yasui, Takuya; Yoshioka, Masahito; Mohd. Yamin, Bohari; Utimoto, Kiitiro; Oshima, Koichiro.

In: Chirality, Vol. 15, No. 1, 2003, p. 38-40.

Research output: Contribution to journalArticle

Matsubara, S, Kasuga, Y, Yasui, T, Yoshioka, M, Mohd. Yamin, B, Utimoto, K & Oshima, K 2003, 'Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives', Chirality, vol. 15, no. 1, pp. 38-40. https://doi.org/10.1002/chir.10147
Matsubara S, Kasuga Y, Yasui T, Yoshioka M, Mohd. Yamin B, Utimoto K et al. Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives. Chirality. 2003;15(1):38-40. https://doi.org/10.1002/chir.10147
Matsubara, Seijiro ; Kasuga, Yuri ; Yasui, Takuya ; Yoshioka, Masahito ; Mohd. Yamin, Bohari ; Utimoto, Kiitiro ; Oshima, Koichiro. / Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives. In: Chirality. 2003 ; Vol. 15, No. 1. pp. 38-40.
@article{a531be2995fe4b888a2be5cb6a6fb049,
title = "Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives",
abstract = "Both enantiomers of 3-hydroxyalkanoates and -alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and α-bromoamide is also discussed.",
keywords = "Aldol, Diastereoselective, Enolate, Samarium",
author = "Seijiro Matsubara and Yuri Kasuga and Takuya Yasui and Masahito Yoshioka and {Mohd. Yamin}, Bohari and Kiitiro Utimoto and Koichiro Oshima",
year = "2003",
doi = "10.1002/chir.10147",
language = "English",
volume = "15",
pages = "38--40",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "1",

}

TY - JOUR

T1 - Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives

AU - Matsubara, Seijiro

AU - Kasuga, Yuri

AU - Yasui, Takuya

AU - Yoshioka, Masahito

AU - Mohd. Yamin, Bohari

AU - Utimoto, Kiitiro

AU - Oshima, Koichiro

PY - 2003

Y1 - 2003

N2 - Both enantiomers of 3-hydroxyalkanoates and -alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and α-bromoamide is also discussed.

AB - Both enantiomers of 3-hydroxyalkanoates and -alkanones were prepared by the diastereocontrolled addition of enolates to ketones containing (R)-6-methyl-1,3-oxathiane moiety as a chiral auxiliary; a formation of enolate from samarium(II) iodide and α-bromoamide is also discussed.

KW - Aldol

KW - Diastereoselective

KW - Enolate

KW - Samarium

UR - http://www.scopus.com/inward/record.url?scp=0037215470&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037215470&partnerID=8YFLogxK

U2 - 10.1002/chir.10147

DO - 10.1002/chir.10147

M3 - Article

C2 - 12467041

AN - SCOPUS:0037215470

VL - 15

SP - 38

EP - 40

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 1

ER -