TY - JOUR
T1 - Lithiation and stereoselective transformations of 3-aroyl-2,2,4,4tetramethyloxazolidines (TMO amides), a new class of acid-labile atropisomeric amides
AU - Anstiss, Mark
AU - Clayden, Jonathan
AU - Grube, Alexander
AU - Youssef, Latifa H.
PY - 2002/2
Y1 - 2002/2
N2 - Aromatic amides 4 (3-aroyl-2,2,4,4-tetramethyloxazolidines or TMO amides) derived by acylation of 2,2,4,4-tetramethyloxazolidine 6 undergo ortho- and lateral lithiation reactions. Given sufficient steric hindrance to bond rotation, they exhibit atropisomerism about the Ar-CO bond and the Ar-CO axis is able to control the atroposelective formation of new stereogenic centres. Unlike amides derived from hindered secondary amines such as diisopropylamine, the 3-aroyl-2,2,4,4-tetramethyloxazolidines are acid-sensitive, and treatment with methanesulfonic acid gives lactones or lactams by cyclisation onto the amide group.
AB - Aromatic amides 4 (3-aroyl-2,2,4,4-tetramethyloxazolidines or TMO amides) derived by acylation of 2,2,4,4-tetramethyloxazolidine 6 undergo ortho- and lateral lithiation reactions. Given sufficient steric hindrance to bond rotation, they exhibit atropisomerism about the Ar-CO bond and the Ar-CO axis is able to control the atroposelective formation of new stereogenic centres. Unlike amides derived from hindered secondary amines such as diisopropylamine, the 3-aroyl-2,2,4,4-tetramethyloxazolidines are acid-sensitive, and treatment with methanesulfonic acid gives lactones or lactams by cyclisation onto the amide group.
KW - Amides
KW - Atropisomerism
KW - Lactones
KW - Lithiation
KW - Stereoselectivity
UR - http://www.scopus.com/inward/record.url?scp=0036172663&partnerID=8YFLogxK
U2 - 10.1055/s-2002-19748
DO - 10.1055/s-2002-19748
M3 - Article (Academic Journal)
AN - SCOPUS:0036172663
SN - 0936-5214
SP - 290
EP - 294
JO - Synlett
JF - Synlett
IS - 2
ER -