Stereocontrolled preparation of 1,2-diol with quaternary chiral center

Yoshihisa Murata; Tomoyuki Kamino; Seijiro Hosokawa; Susumu Kobayashi

doi:10.1016/S0040-4039(02)01946-9

Stereocontrolled preparation of 1,2-diol with quaternary chiral center

Yoshihisa Murata, Tomoyuki Kamino, Seijiro Hosokawa, Susumu Kobayashi^*

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion.

Original language	English
Pages (from-to)	8121-8123
Number of pages	3
Journal	Tetrahedron Letters
Volume	43
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4039(02)01946-9
Publication status	Published - 2002 Nov 4
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Stereocontrolled preparation of 1,2-diol with quaternary chiral center",

abstract = "Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion.",

author = "Yoshihisa Murata and Tomoyuki Kamino and Seijiro Hosokawa and Susumu Kobayashi",

note = "Funding Information: This work was financially supported in part by Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology.",

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T1 - Stereocontrolled preparation of 1,2-diol with quaternary chiral center

AU - Murata, Yoshihisa

AU - Kamino, Tomoyuki

AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

N1 - Funding Information: This work was financially supported in part by Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology.

PY - 2002/11/4

Y1 - 2002/11/4

N2 - Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion.

AB - Development of an enantio- and stereoselective construction of 1,2-diols including a quaternary chiral center was achieved by a titanium-mediated aldol reaction of lactates bearing chiral oxazolidine-2-ones. anti-Aldol and syn-aldol were selectively obtained by the choice of a benzyl and TBS protecting group, respectively. Plausible transition states are also shown based on the stereochemistry of the enolate anion.

UR - http://www.scopus.com/inward/record.url?scp=0037020645&partnerID=8YFLogxK

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U2 - 10.1016/S0040-4039(02)01946-9

DO - 10.1016/S0040-4039(02)01946-9

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SN - 0040-4039

VL - 43

SP - 8121

EP - 8123

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Stereocontrolled preparation of 1,2-diol with quaternary chiral center

Abstract

ASJC Scopus subject areas

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