TY - JOUR
T1 - New Chiral Auxiliaries for Enolate Alkylations
AU - Jeong, Kyu‐Sung ‐S
AU - Parris, Kevin
AU - Ballester, Pablo
AU - Rebek, Julius
PY - 1990/5
Y1 - 1990/5
N2 - The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R Me, E PhCH2, or R PhCH2, E Me). (Figure Presented.)
AB - The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R Me, E PhCH2, or R PhCH2, E Me). (Figure Presented.)
UR - http://www.scopus.com/inward/record.url?scp=33748216006&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33748216006&partnerID=8YFLogxK
U2 - 10.1002/anie.199005551
DO - 10.1002/anie.199005551
M3 - Article
AN - SCOPUS:33748216006
VL - 29
SP - 555
EP - 556
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 5
ER -