Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones

Tatsuhiko Yoshino; Hiroyuki Morimoto; Gang Lu; Shigeki Matsunaga; Masakatsu Shibasaki

doi:10.1021/ja908571w

Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones

Tatsuhiko Yoshino, Hiroyuki Morimoto, Gang Lu, Shigeki Matsunaga, Masakatsu Shibasaki

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

114 被引用数 (Scopus)

抄録

(Chemical Equation Presented) Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-substituted α-isothiocyanato esters with unactivated simple ketones is described. A Bu₂Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected α-amino-β-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.

本文言語	英語
ページ（範囲）	17082-17083
ページ数	2
ジャーナル	Journal of the American Chemical Society
巻	131
号	47
DOI	https://doi.org/10.1021/ja908571w
出版ステータス	出版済み - 12月 2 2009
外部発表	はい

!!!All Science Journal Classification (ASJC) codes

触媒
化学 (全般)
生化学
コロイド化学および表面化学

文献へのアクセス

10.1021/ja908571w

他のファイルとリンク

フィンガープリント

「Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones. / Yoshino, Tatsuhiko; Morimoto, Hiroyuki; Lu, Gang その他.

In: Journal of the American Chemical Society, Vol. 131, No. 47, 02.12.2009, p. 17082-17083.

研究成果: ジャーナルへの寄稿 › 学術誌 › 査読

@article{bb69195156014c73b8f495818a67c22f,

title = "Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones",

abstract = "(Chemical Equation Presented) Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-substituted α-isothiocyanato esters with unactivated simple ketones is described. A Bu2Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected α-amino-β-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.",

author = "Tatsuhiko Yoshino and Hiroyuki Morimoto and Gang Lu and Shigeki Matsunaga and Masakatsu Shibasaki",

year = "2009",

month = dec,

day = "2",

doi = "10.1021/ja908571w",

language = "English",

volume = "131",

pages = "17082--17083",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "47",

}

TY - JOUR

T1 - Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-isothiocyanato esters with ketones

AU - Yoshino, Tatsuhiko

AU - Morimoto, Hiroyuki

AU - Lu, Gang

AU - Matsunaga, Shigeki

AU - Shibasaki, Masakatsu

PY - 2009/12/2

Y1 - 2009/12/2

N2 - (Chemical Equation Presented) Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-substituted α-isothiocyanato esters with unactivated simple ketones is described. A Bu2Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected α-amino-β-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.

AB - (Chemical Equation Presented) Construction of contiguous tetrasubstituted chiral carbon stereocenters via direct catalytic asymmetric aldol reaction of α-substituted α-isothiocyanato esters with unactivated simple ketones is described. A Bu2Mg/Schiff base catalyst promoted the aldol addition/cyclization sequence at room temperature, giving protected α-amino-β-hydroxy esters with contiguous tetrasubstituted chiral carbon stereocenters in 99 to 68% yield, 98:2 to 74:26 dr, and 98 to 82% ee.

UR - http://www.scopus.com/inward/record.url?scp=72249092076&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=72249092076&partnerID=8YFLogxK

U2 - 10.1021/ja908571w

DO - 10.1021/ja908571w

M3 - Article

C2 - 19894736

AN - SCOPUS:72249092076

VL - 131

SP - 17082

EP - 17083

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 47

ER -