Efficient 1,8- To 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary

Yasufunii Taniai; Tetsutaro Hattori; Masaniitsu Date; Hidcki Takayama; Yoshinori Kamikubo; Yuji Minato; Sotaro Miyano

Efficient 1,8- To 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary

Yasufunii Taniai, Tetsutaro Hattori, Masaniitsu Date, Hidcki Takayama, Yoshinori Kamikubo, Yuji Minato, Sotaro Miyano

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

Abstract

Efficient diastereoselective alkylation of 6- and £-keto acids with Grignard reagents was achieved in up to 97% de by conversion into the : 2′-[3-(2-methoxyethoxy)propoxy]-(1,1′-binaphthyl)-2-ol esters, while the corresponding alkylation of ζ- to θ-keto acids could effectively be carried out in up to 88% de by simply using BINOL as the chiral auxiliary.

Original language	English
Pages (from-to)	1141-1142
Number of pages	2
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	9
Publication status	Published - 1999
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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Efficient 1,8- To 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary. / Taniai, Yasufunii; Hattori, Tetsutaro; Date, Masaniitsu et al.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 9, 1999, p. 1141-1142.

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

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abstract = "Efficient diastereoselective alkylation of 6- and £-keto acids with Grignard reagents was achieved in up to 97% de by conversion into the : 2′-[3-(2-methoxyethoxy)propoxy]-(1,1′-binaphthyl)-2-ol esters, while the corresponding alkylation of ζ- to θ-keto acids could effectively be carried out in up to 88% de by simply using BINOL as the chiral auxiliary.",

author = "Yasufunii Taniai and Tetsutaro Hattori and Masaniitsu Date and Hidcki Takayama and Yoshinori Kamikubo and Yuji Minato and Sotaro Miyano",

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T1 - Efficient 1,8- To 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary

AU - Taniai, Yasufunii

AU - Hattori, Tetsutaro

AU - Date, Masaniitsu

AU - Takayama, Hidcki

AU - Kamikubo, Yoshinori

AU - Minato, Yuji

AU - Miyano, Sotaro

PY - 1999

Y1 - 1999

N2 - Efficient diastereoselective alkylation of 6- and £-keto acids with Grignard reagents was achieved in up to 97% de by conversion into the : 2′-[3-(2-methoxyethoxy)propoxy]-(1,1′-binaphthyl)-2-ol esters, while the corresponding alkylation of ζ- to θ-keto acids could effectively be carried out in up to 88% de by simply using BINOL as the chiral auxiliary.

AB - Efficient diastereoselective alkylation of 6- and £-keto acids with Grignard reagents was achieved in up to 97% de by conversion into the : 2′-[3-(2-methoxyethoxy)propoxy]-(1,1′-binaphthyl)-2-ol esters, while the corresponding alkylation of ζ- to θ-keto acids could effectively be carried out in up to 88% de by simply using BINOL as the chiral auxiliary.

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JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 9

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Efficient 1,8- To 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary

Abstract

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