Chiral Lewis base-assisted Brønsted acid (LBBA)-catalyzed enantioselective cyclization of 2-geranylphenols

Akira Sakakura; Masayuki Sakuma; Kazuaki Ishihara

doi:10.1021/ol201032t

Chiral Lewis base-assisted Brønsted acid (LBBA)-catalyzed enantioselective cyclization of 2-geranylphenols

Akira Sakakura, Masayuki Sakuma, Kazuaki Ishihara

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

48 Citations (Scopus)

Abstract

Chiral Lewis base-assisted Brønsted acids (Chiral LBBAs) have been designed as new organocatalysts for biomimetic enantioselective cyclization. A salt of a chiral phosphonous acid diester with FSO₃H catalyzes the enantioselective cyclization of 2-geranylphenols to give the desired trans-fused cyclized products with high diastereo- and enantioselectivities (up to 98:2 dr and 93% ee).

Original language	English
Pages (from-to)	3130-3133
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	12
DOIs	https://doi.org/10.1021/ol201032t
Publication status	Published - Jun 17 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol201032t

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abstract = "Chiral Lewis base-assisted Br{\o}nsted acids (Chiral LBBAs) have been designed as new organocatalysts for biomimetic enantioselective cyclization. A salt of a chiral phosphonous acid diester with FSO3H catalyzes the enantioselective cyclization of 2-geranylphenols to give the desired trans-fused cyclized products with high diastereo- and enantioselectivities (up to 98:2 dr and 93% ee).",

author = "Akira Sakakura and Masayuki Sakuma and Kazuaki Ishihara",

year = "2011",

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doi = "10.1021/ol201032t",

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AU - Sakakura, Akira

AU - Sakuma, Masayuki

AU - Ishihara, Kazuaki

PY - 2011/6/17

Y1 - 2011/6/17

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AB - Chiral Lewis base-assisted Brønsted acids (Chiral LBBAs) have been designed as new organocatalysts for biomimetic enantioselective cyclization. A salt of a chiral phosphonous acid diester with FSO3H catalyzes the enantioselective cyclization of 2-geranylphenols to give the desired trans-fused cyclized products with high diastereo- and enantioselectivities (up to 98:2 dr and 93% ee).

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JF - Organic Letters

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Chiral Lewis base-assisted Brønsted acid (LBBA)-catalyzed enantioselective cyclization of 2-geranylphenols

Abstract

ASJC Scopus subject areas

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