Direct Catalytic Enantio- And Diastereoselective Aldol Reaction Using a Zn-Zn-Linked-BINOL Complex

A Practical Synthesis of syn-1,2-Diols

Naoya Kumagai, Shigeki Matsunaga, Naoki Yoshikawa, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticle

108 Citations (Scopus)

Abstract

matrix presented The direct catalytic enantio- and diastereoselective aldol reaction with 2-hydroxy-2′-methoxyacetophenone proceeded smoothly using as little as 1 mol % of a dinuclear zinc catalyst, Zn-Zn-linked-BINOL complex 2, to afford α,β-dihydroxy ketones in a highly syn-selective manner (up to synlanti 97/3) and in excellent yields (up to 95%) and ees (up to 99%). Efficient transformations of the α,β-dihydroxy ketone into an α,β-dihydroxy ester and an α,β-dihydroxy amide via regioselective rearrangements are also described.

Original languageEnglish
Pages (from-to)1539-1542
Number of pages4
JournalOrganic Letters
Volume3
Issue number10
DOIs
Publication statusPublished - May 17 2001

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Ketones
ketones
synthesis
Amides
amides
Zinc
esters
Esters
zinc
catalysts
Catalysts
matrices
naphthol BINOL
3-hydroxybutanal
2'-methoxyacetophenone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Direct Catalytic Enantio- And Diastereoselective Aldol Reaction Using a Zn-Zn-Linked-BINOL Complex : A Practical Synthesis of syn-1,2-Diols. / Kumagai, Naoya; Matsunaga, Shigeki; Yoshikawa, Naoki; Ohshima, Takashi; Shibasaki, Masakatsu.

In: Organic Letters, Vol. 3, No. 10, 17.05.2001, p. 1539-1542.

Research output: Contribution to journalArticle

Kumagai, Naoya ; Matsunaga, Shigeki ; Yoshikawa, Naoki ; Ohshima, Takashi ; Shibasaki, Masakatsu. / Direct Catalytic Enantio- And Diastereoselective Aldol Reaction Using a Zn-Zn-Linked-BINOL Complex : A Practical Synthesis of syn-1,2-Diols. In: Organic Letters. 2001 ; Vol. 3, No. 10. pp. 1539-1542.
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