Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions.
An indene-based thiazolidinethione chiral auxiliary was prepared in two steps from trans-1-amino-2-indanol. Chlorotitanium enolates of this chiral auxiliary delivered excellent diastereoselectivities in propionate and acetate aldol additions. The chiral auxiliary was easily removed to deliver several valuable functionalities.
Osorio-Lozada
Antonio
A
Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA.
Olivo
Horacio F
HF
D000085:Acetates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D007189:Indans / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000737:chemistry
D000085:Acetates; D000447:Aldehydes; D007189:Indans; D007192:Indenes; D011422:Propionates; D053778:Thiazolidines; C116915:aminoindanol; C033089:thiazoline-2-thione; C116609:3-hydroxybutanal