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^*

^*この研究の対応する著者

研究成果: Article › 査読

31 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	8121-8123
ページ数	3
ジャーナル	Tetrahedron Letters
巻	43
号	45
DOI	https://doi.org/10.1016/S0040-4039(02)01946-9
出版ステータス	Published - 2002 11月 4
外部発表	はい

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4039(02)01946-9

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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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doi = "10.1016/S0040-4039(02)01946-9",

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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.

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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

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