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. Author manuscript; available in PMC: 2014 May 28.
Published in final edited form as: Org Biomol Chem. 2013 May 28;11(20):3400–3408. doi: 10.1039/c3ob40251g

Table 3.

Asymmetric addition of lithium enolates of different 2-bromoacetates onto N,N-diisopropylphosphonyl benzaldiminea

graphic file with name nihms464544t40.jpg

Entry R Product Yield(%)b drc,d
1 Ethyl graphic file with name nihms464544t41.jpg 78 99.4:0.6
2 Isopropyl graphic file with name nihms464544t42.jpg 77 >99:1
3 tert-Butyl graphic file with name nihms464544t43.jpg 74 >99:1
a

Reaction conditions: 0.57 mmol imine, 1.15 mmol methyl-2-bromo acetate, 1.20mmol LiHMDS 14 mL solvent, −78 °C.

b

Isolated yield of the pure product.

c

Diastereoselectivities were determined by 31P-NMR analysis of crude products.

d

>99:1 means only one isomer was observed by 31P NMR.