Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols

Takuya Kochi; Tony P. Tang; Jonathan A. Ellman

doi:10.1021/ja0363462

Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols

Takuya Kochi, Tony P. Tang, Jonathan A. Ellman

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98 Citations (Scopus)

Abstract

A general method is described for asymmetric synthesis of both syn- and anti-1,3-amino alcohols. The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. The reduction of the product β-hydroxy N-sulfinyl imines 2 with catecholborane and LiBHEt₃ provides syn- and anti-1,3-amino alcohols with very high diastereomeric ratios. This method was found to be effective for a variety of substrates incorporating either aromatic or various aliphatic substituents. The convergent and efficient asymmetric syntheses of the two natural products, (-)-8-epihalosaline and (-)-halosaline, were also accomplished.

Original language	English
Pages (from-to)	11276-11282
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	125
Issue number	37
DOIs	https://doi.org/10.1021/ja0363462
Publication status	Published - 2003 Sept 17
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "A general method is described for asymmetric synthesis of both syn- and anti-1,3-amino alcohols. The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. The reduction of the product β-hydroxy N-sulfinyl imines 2 with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohols with very high diastereomeric ratios. This method was found to be effective for a variety of substrates incorporating either aromatic or various aliphatic substituents. The convergent and efficient asymmetric syntheses of the two natural products, (-)-8-epihalosaline and (-)-halosaline, were also accomplished.",

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AU - Ellman, Jonathan A.

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AB - A general method is described for asymmetric synthesis of both syn- and anti-1,3-amino alcohols. The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. The reduction of the product β-hydroxy N-sulfinyl imines 2 with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohols with very high diastereomeric ratios. This method was found to be effective for a variety of substrates incorporating either aromatic or various aliphatic substituents. The convergent and efficient asymmetric syntheses of the two natural products, (-)-8-epihalosaline and (-)-halosaline, were also accomplished.

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Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols

Abstract

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