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. 2021 May 5;363(12):3138–3143. doi: 10.1002/adsc.202100037

Table 2.

Screening of different chiral phosphoric acid (CPA) catalysts.

graphic file with name ADSC-363-3138-g002.jpg

Entry

Chiral Phosphoric Acid (CPA)

Conv. [%][a]

ee [%][b]

1

(S)‐11

>99

<1

2

(R)‐12

>99

17[c]

3

(S)‐13

>99

27

4

(S)‐15

>99

33[d]

5

(R)‐14

>99

44[c]

6

(S)‐9

>99

70

Reaction conditions: ketone (0.1 mmol), zinc (5 eq.), NH4Cl (8 eq.), CPA (10 mol‐%), 7 b (1.5 eq.) in toluene (1 mL) and cyclohexane (1 mL); spontaneous lactonization to product 10 b was observed for all entries.

[a] Conversions were determined via HPLC‐UV (215 nm).

[b] The enantiomeric excess was determined on a chiral stationary phase via normal phase HPLC‐UV (215 nm).

[c] The opposite enantiomer was observed [note: the (R)‐CPA has been used in case of these entries].

[d] The opposite enantiomer was observed [note: reagent 7d was used in case of this entry].