Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction: A highly efficient route to cis-1,3-disubstituted tetrahydro-β-carbolines

Patrick D. Bailey; Madeleine H. Moore; Keith M. Morgan; David I. Smith; John M. Vernon

doi:10.1016/S0040-4039(00)73247-3

Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction: A highly efficient route to cis-1,3-disubstituted tetrahydro-β-carbolines

Patrick D. Bailey
, Madeleine H. Moore
, Keith M. Morgan
, David I. Smith
, John M. Vernon

School of Engineering & Physical Sciences

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

40 Citations (Scopus)

Abstract

Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spengler reaction between tryptophan esters and aldehydes can be controlled by varying the size of the ester group; the reaction proceeds in essentially quantitative yield with most aldehydes when conducted in chloroform in the presence of molecular sieves.

Original language	English
Pages (from-to)	3587-3588
Number of pages	2
Journal	Tetrahedron Letters
Volume	35
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)73247-3
Publication status	Published - 1994

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title = "Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction: A highly efficient route to cis-1,3-disubstituted tetrahydro-β-carbolines",

abstract = "Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spengler reaction between tryptophan esters and aldehydes can be controlled by varying the size of the ester group; the reaction proceeds in essentially quantitative yield with most aldehydes when conducted in chloroform in the presence of molecular sieves.",

author = "Bailey, \{Patrick D.\} and Moore, \{Madeleine H.\} and Morgan, \{Keith M.\} and Smith, \{David I.\} and Vernon, \{John M.\}",

year = "1994",

doi = "10.1016/S0040-4039(00)73247-3",

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volume = "35",

pages = "3587--3588",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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T1 - Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction

T2 - A highly efficient route to cis-1,3-disubstituted tetrahydro-β-carbolines

AU - Bailey, Patrick D.

AU - Moore, Madeleine H.

AU - Morgan, Keith M.

AU - Smith, David I.

AU - Vernon, John M.

PY - 1994

Y1 - 1994

N2 - Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spengler reaction between tryptophan esters and aldehydes can be controlled by varying the size of the ester group; the reaction proceeds in essentially quantitative yield with most aldehydes when conducted in chloroform in the presence of molecular sieves.

AB - Under conditions of kinetic control, the cis-diastereoselectivity of the Pictet-Spengler reaction between tryptophan esters and aldehydes can be controlled by varying the size of the ester group; the reaction proceeds in essentially quantitative yield with most aldehydes when conducted in chloroform in the presence of molecular sieves.

U2 - 10.1016/S0040-4039(00)73247-3

DO - 10.1016/S0040-4039(00)73247-3

M3 - Article

SN - 0040-4039

VL - 35

SP - 3587

EP - 3588

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Enhancing the yield and diastereoselectivity of the Pictet-Spengler reaction: A highly efficient route to cis-1,3-disubstituted tetrahydro-β-carbolines

Abstract

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