Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates

Kyosuke Tanaka, Yukiko Fujimori, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

(Chemical Equation Presented) The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium (E)- crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.

Original languageEnglish
Pages (from-to)6292-6298
Number of pages7
JournalJournal of Organic Chemistry
Volume73
Issue number16
DOIs
Publication statusPublished - 2008 Aug 15

Fingerprint

Potassium
Functional groups
Substrates
propionaldehyde

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. / Tanaka, Kyosuke; Fujimori, Yukiko; Saikawa, Yoko; Nakata, Masaya.

In: Journal of Organic Chemistry, Vol. 73, No. 16, 15.08.2008, p. 6292-6298.

Research output: Contribution to journalArticle

@article{5eb76f1edd5c44958daf9ffee3e92fcb,
title = "Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates",
abstract = "(Chemical Equation Presented) The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium (E)- crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.",
author = "Kyosuke Tanaka and Yukiko Fujimori and Yoko Saikawa and Masaya Nakata",
year = "2008",
month = "8",
day = "15",
doi = "10.1021/jo801106b",
language = "English",
volume = "73",
pages = "6292--6298",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - Diastereoselective synthesis of useful building blocks by crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates

AU - Tanaka, Kyosuke

AU - Fujimori, Yukiko

AU - Saikawa, Yoko

AU - Nakata, Masaya

PY - 2008/8/15

Y1 - 2008/8/15

N2 - (Chemical Equation Presented) The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium (E)- crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.

AB - (Chemical Equation Presented) The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of β-branched α-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium (E)- crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.

UR - http://www.scopus.com/inward/record.url?scp=50149093469&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=50149093469&partnerID=8YFLogxK

U2 - 10.1021/jo801106b

DO - 10.1021/jo801106b

M3 - Article

C2 - 18630883

AN - SCOPUS:50149093469

VL - 73

SP - 6292

EP - 6298

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 16

ER -