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Complete π‐Facial Stereoselectivity in the TiCl 4 ‐Mediated [4 + 2] Cycloaddition of Cyclopentadiene to N , N ′‐fumaroyldi[(2 R )‐bornane‐10,2‐sultam]
Author(s) -
Chapius Christian,
Rzepecki Piotr,
Bauer Tomasz,
Jurczak Janusz
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780114
Subject(s) - chemistry , cyclopentadiene , cycloaddition , stereoselectivity , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Under the co‐operative influence of two prosthetic groups, and independent of the TiCl 4 concentration, complete and constant diastereofacial π‐selection was achieved during the [4 + 2] cycloaddition of cyclopentadiene to N , N ′‐fumaroyl‐di[(2 R )‐bornane‐10,2‐sultam] ((−)‐ 1c ); reactive conformations are discussed.