A. Evans Enantioselective C=O Addition: Catalyst Scope Chem 115 Representative Reduction The catalyst (R)cat (0. 2 equiv) (S)cat(0.1 equiv) 1.5 equiv HO 92%ee n-C5Hl1 ret.Let1992.33,2319 n-CsHl1 THF 23%C 2 min Arco Fluoxetine( Prozac) Synthesis (R)-cat, as above 94%ee>99‰) Corey,JAcs1987,109,7925 0. 1 equiv Tet Let1989,30.5207 Prozac③ i An a-Amino Acid Synthesis 91%ee nC5H1195% c-C6H1192% t-C4Hg 98% (S) 0. 1 equiv n-Bu Corey,JAcs1992,114,1906 Tet.Let1992,33,3435 Tet. Let1992,33,3431 CCl3 N3 m temp 19A-08-Corey Cat 1/19/00 1: 48 PMD. A. Evans Enantioselective C=O Addition: Catalyst Scope Chem 115 Representative Reductions 90 : 10 91 : 9 (R)-cat, as above (S) cat (0.1 equiv) BH3 (0.6 equiv) THF 23°C, 2 min The catalyst Corey, JACS 1987, 109, 7925 (S) cat BH3 86% ee 91% ee BH3 (S) cat 91% ee BH3 (S) cat (R) cat (0.2 equiv) 1.5 equiv 92% ee Tet. Let 1992, 33, 2319 Fluoxetine (Prozac®) Synthesis BH3 94% ee (>99%) 0.1 equiv Na –I MeNH2 NaH Prozac® An α-Amino Acid Synthesis Tet. Let 1989, 30, 5207 0.1 equiv R ee n-C5H11 95% c-C6H11 92% t-C4H9 98% HO– N3 – rm temp Corey, JACS 1992, 114, 1906 Tet. Let 1992, 33, 3435 Tet. Let 1992, 33, 3431 Me Me O Me Me Me Me Me Me Me Me Me N B O Ph Ph H Me O O n-C5H11 O ArCOO ArCOO OH n-C5H11 O O Me Me Me HO Me Me O BH O F F Cl O N O O n-C5H11 OH ArCOO O OH Br O OH Br Me O OH Me B O Ph Ph H Me OH Cl NHMe OH O NHMe CF3 CF3 Cl CCl R 3 O OH R CCl3 B n-Bu H Ph Ph N O O BH O CCl R 3 OH N3 R COOH 19A-08-Corey Cat 1/19/00 1:48 PM