Chiral aggregates and asymmetric induction of the reduction of prochiral ketones.

Abstract:

:The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral ketones by NaBH(4), in contrast with dendrimers bearing the same types of sugar moieties, which gave more than 50% ee under the same reaction conditions. Moreover, in the presence of neoglycodendrimers in THF we have been able to improve reduction of prochiral ketones to give very high stereoselectivity, near 100% in many cases. Comparison of these results suggests that to improve high stereoselectivity it is necessary to work with rigid, well-organized colloidal objects. Copyright 2000 Wiley-Liss, Inc.

journal_name

Chirality

journal_title

Chirality

authors

Rico-Lattes I I,Schmitzer A,Perez E,Lattes A

doi

10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2

subject

Has Abstract

pub_date

2001-01-01 00:00:00

pages

24-28

issue

1

eissn

0899-0042

issn

1520-636X

pii

10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2

journal_volume

13

pub_type

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