TY - JOUR
T1 - Diastereo- and enantio-selectivity in the Pictet-Spengler reaction
AU - Bailey, Patrick D.
AU - Hollinshead, Sean P.
AU - McLay, Neil R.
AU - Morgan, Keith
AU - Palmer, Sarah J.
AU - Prince, Stephen N.
AU - Reynolds, Colin D.
AU - Wood, Stephen D.
PY - 1993
Y1 - 1993
N2 - The factors that control the relative and absolute stereochemistry of 1,3-disubstituted and 1,2,3-trisubstituted tetrahydro-ß-carbolines formed via the Pictet-Spengler reaction are discussed. In particular, the stereochemical factors that lead to the predominance of cis-1,3-disubstituted products under conditions of kinetic control are presented, with the aid of X-ray crystallographic data on a number of compounds; methods for assigning relative stereochemistry on the basis of NMR data are given; the mechanism by which racemisation can occur during the Pictet-Spengler reaction has also been studied, and procedures for eliminating this problem are given.
AB - The factors that control the relative and absolute stereochemistry of 1,3-disubstituted and 1,2,3-trisubstituted tetrahydro-ß-carbolines formed via the Pictet-Spengler reaction are discussed. In particular, the stereochemical factors that lead to the predominance of cis-1,3-disubstituted products under conditions of kinetic control are presented, with the aid of X-ray crystallographic data on a number of compounds; methods for assigning relative stereochemistry on the basis of NMR data are given; the mechanism by which racemisation can occur during the Pictet-Spengler reaction has also been studied, and procedures for eliminating this problem are given.
UR - http://www.scopus.com/inward/record.url?scp=37049086632&partnerID=8YFLogxK
U2 - 10.1039/P19930000431
DO - 10.1039/P19930000431
M3 - Article
SN - 1472-7781
SP - 431
EP - 439
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 4
ER -