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Non-chelate control is generally difficult to realize. With the carbenoid 2 it has now been possible for the first time to carry out such an addition (85 % de) of an organolithium compound to the protected lactaldehyde (S)-1. A chiral 1 bromo-l-lithio-l-alkene increases the diastereoselectivity to 95 % de. The product 4 separated the formal after dehalogenation and ozonolysis is formed by the formal addition of ⊖CH2OH.
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Braun et al. (1989) studied this question.
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