Supporting Information-II. Asymmetric Synthesis of Drug-like Spiro[chroman-3,3'- indolin]-2'-ones through Aminal-catalysis
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information-II Asymmetric Synthesis of Drug-like Spiro[chroman-3,3'- indolin]-2'-ones through Aminal-catalysis D. B. Ramachary,* M. Shiva Prasad, S. Vijaya Laxmi and R. Madhavachary Catalysis Laboratory, School of Chemistry, University of Hyderabad, Central University (P..), Hyderabad , India and General Information: The enantiomeric excess (ee) of the r-m products 5, 7 and 9 was determined by chiral stationary phase HPLC using a Daicel Chiralcel D-H, Chiralcel J-H, Chiralpak AD-H, Chiralpak AS-H, Lux 5u Amylose-2, Lux 5u Cellulose-1, or Lux 5u Cellulose-2 columns and hexane/2-propanol as the eluent. Retention times and solvent ratios are indicated in the respective entries. General ote Regarding HPLC Chromatograms: In all racemic HPLC chromatograms of 7 and 9, only four enantiomeric peaks representing the minor and major diastereomers were labeled with retention times. But many of the chiral HPLC chromatograms of 7 and 9 were represented only major diastereomer with retention times. Very few chiral HPLC chromatograms of 7 were represented both minor and major diastereomers with retention times. S-1
2 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7aa: C 2 Et 7aa Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7aa (99% ee): C 2 Et ( )-7aa Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-2
3 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ab: C 2 Et Ac 7ab Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ab (84% ee): C 2 Et Ac ( )-7ab Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-3
4 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ac: C 2 Et Ts 7ac Daicel Chiralpak AD-H, Hexane/i-PrH = 90:10, Flow Rate 1.0 ml/min, 254 nm CHIRAL-( )-7ac (96% ee): C 2 Et Ts ( )-7ac Daicel Chiralpak AD-H, Hexane/i-PrH = 90:10, Flow Rate 1.0 ml/min, 254 nm S-4
5 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ba: F C 2 Et 7ba Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ba (91% ee): F C 2 Et ( )-7ba Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm S-5
6 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ca: Cl C 2 Et 7ca Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ca (96% ee): Cl C 2 Et ( )-7ca Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-6
7 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7da: Br C 2 Et 7da Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7da (92% ee): Br C 2 Et ( )-7da Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-7
8 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ea: Cl Cl C 2 Et 7ea Daicel Chiralcel D-H, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-(+)-7ea (81% ee): Cl Cl C 2 Et (+)-7ea Daicel Chiralcel D-H, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm S-8
9 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7fa: 2 C 2 Et 7fa Daicel Chiralpak AD-H, Hexane/i-PrH = 97:3, Flow Rate 1.0 ml/min, 254 nm CHIRAL-(+)-7fa [28% ee for major isomer and 96% ee for minor isomer]: 2 C 2 Et (+)-7fa Daicel Chiralpak AD-H, Hexane/i-PrH = 97:3, Flow Rate 1.0 ml/min, 254 nm S-9
10 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ga: Me C 2 Et 7ga Lux 5u Cellulose-1, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ga (93% ee): Me C 2 Et ( )-7ga Lux 5u Cellulose-1, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-10
11 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ha: Me C 2 Et 7ha Daicel Chiralpak AD-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ha (>99% ee): Me C 2 Et ( )-7ha Daicel Chiralpak AD-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-11
12 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ia: H C 2 Et 7ia Lux 5u Cellulose-1, Hexane/i-PrH = 97:3, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ia (98% ee): H C 2 Et ( )-7ia Lux 5u Cellulose-1, Hexane/i-PrH = 97:3, Flow Rate 0.5 ml/min, 254 nm S-12
13 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ja: Me C 2 Et 7ja Daicel Chiralpak AD-H, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ja (96% ee): Me C 2 Et ( )-7ja Daicel Chiralpak AD-H, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm S-13
14 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ka: Me C 2 Et 7ka Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ka (95% ee): Me C 2 Et ( )-7ka Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-14
15 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ge: F 7ge Me C 2 Et Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ge (91% ee): F ( )-7ge Me C 2 Et Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-15
16 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gf: Cl Me C 2 Et 7gf Lux 5u Cellulose-2, Hexane/i-PrH = 90:10, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7gf (94% ee): Cl Me C 2 Et ( )-7gf Lux 5u Cellulose-2, Hexane/i-PrH = 90:10, Flow Rate 0.5 ml/min, 254 nm S-16
17 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gg: Br 7gg Me C 2 Et Lux 5u Cellulose-2, Hexane/i-PrH = 90:10, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7gg (94% ee): Br ( )-7gg Me C 2 Et Lux 5u Cellulose-2, Hexane/i-PrH = 90:10, Flow Rate 0.5 ml/min, 254 nm S-17
18 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gh: 2 Me C 2 Et 7gh Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7gh (96% ee): 2 Me C 2 Et ( )-7gh Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-18
19 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ki: Me 2 C 7ki CH 3 C 2 Et Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7ki (98% ee): Me 2 C ( )-7ki CH 3 C 2 Et Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm S-19
20 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gj: Me 7gj Me C 2Et Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7gj (96% ee): Me Me C 2 Et ( )-7gj Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm S-20
21 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gk: Me Me C 2 Et 7gk Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 1.0 ml/min, 254 nm CHIRAL-( )-7gk (96% ee): Me Me C 2 Et ( )-7gk Lux 5u Cellulose-2, Hexane/i-PrH = 98:2, Flow Rate 1.0 ml/min, 254 nm S-21
22 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7kk: Me 7kk Me C 2 Et Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7kk (96% ee): Me ( )-7kk Me C 2 Et Lux 5u Cellulose-2, Hexane/i-PrH = 95:5, Flow Rate 0.5 ml/min, 254 nm S-22
23 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gl: Me C 2 Et 7gl Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7gl (98% ee): Me C 2 Et ( )-7gl Daicel Chiralcel D-H, Hexane/i-PrH = 98:2, Flow Rate 0.5 ml/min, 254 nm S-23
24 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gm: Me Me C 2 Et 7gm Lux 5u Amylose-2, Hexane/i-PrH = 99.4:0.6, Flow Rate 1.0 ml/min, 220 nm CHIRAL-( )-7gm (94% ee): Me Me C 2 Et ( )-7gm Lux 5u Amylose-2, Hexane/i-PrH = 99.4:0.6, Flow Rate 1.0 ml/min, 200 nm S-24
25 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7gn: Me Me C 2 Et 7gn Lux 5u Amylose-2, Hexane/i-PrH = 98.5:1.5, Flow Rate 0.5 ml/min, 254 nm CHIRAL-( )-7gn (96% ee): Me Me C 2 Et ( )-7gn Lux 5u Amylose-2, Hexane/i-PrH = 98.5:1.5, Flow Rate 0.5 ml/min, 254 nm S-25
26 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7ao: Et 2 C C 2 Et 7ao Daicel Chiralpak AD-H, Hexane/i-PrH = 95:5, Flow Rate 1.0 ml/min, 254 nm CHIRAL-( )-7ao (94% ee): Et 2 C C 2 Et ( )-7ao Daicel Chiralpak AD-H, Hexane/i-PrH = 95:5, Flow Rate 1.0 ml/min, 254 nm S-26
27 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 7kp: Et 2 C F 7kp Me C 2 Et Daicel Chiralpak AD-H, Hexane/i-PrH = 97:3, Flow Rate 1.0 ml/min, 254 nm CHIRAL-( )-7kp (92% ee): Et 2 C F ( )-7kp Me C 2 Et Daicel Chiralpak AD-H, Hexane/i-PrH = 97:3, Flow Rate 1.0 ml/min, 254 nm S-27
28 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry RACEMIC 9aa: Ph 9aa C C Daicel Chiralcel D-H, Hexane/i-PrH = 95:5, Flow Rate 0.6 ml/min, 254 nm CHIRAL-(+)-9aa (98% ee): Ph (+)-9aa C C Daicel Chiralcel D-H, Hexane/i-PrH = 95:5, Flow Rate 0.6 ml/min, 254 nm S-28
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