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

Research output: Contribution to journalArticle

143 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 languageEnglish
Pages (from-to)11276-11282
Number of pages7
JournalJournal of the American Chemical Society
Volume125
Issue number37
DOIs
Publication statusPublished - 2003 Sep 17
Externally publishedYes

Fingerprint

Amino alcohols
Amino Alcohols
Imines
Biological Products
Aldehydes
Substrates
8-epihalosaline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols. / Kochi, Takuya; Tang, Tony P.; Ellman, Jonathan A.

In: Journal of the American Chemical Society, Vol. 125, No. 37, 17.09.2003, p. 11276-11282.

Research output: Contribution to journalArticle

@article{7b275f8915ac4b9480e0636478e1c8b0,
title = "Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols",
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.",
author = "Takuya Kochi and Tang, {Tony P.} and Ellman, {Jonathan A.}",
year = "2003",
month = "9",
day = "17",
doi = "10.1021/ja0363462",
language = "English",
volume = "125",
pages = "11276--11282",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "37",

}

TY - JOUR

T1 - Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols

AU - Kochi, Takuya

AU - Tang, Tony P.

AU - Ellman, Jonathan A.

PY - 2003/9/17

Y1 - 2003/9/17

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0042693200&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042693200&partnerID=8YFLogxK

U2 - 10.1021/ja0363462

DO - 10.1021/ja0363462

M3 - Article

C2 - 16220949

AN - SCOPUS:0042693200

VL - 125

SP - 11276

EP - 11282

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 37

ER -