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Synlett 2003(9): 1279-1282
DOI: 10.1055/s-2003-40347
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Highly Efficient and Stereoselective Synthesis of Polyhydroxylated Pyrrolidines via Regioselective Asymmetric Aminohydroxylation (RAA) and Intramolecular Amidomercuration Reactions

Satwinder Singh, Dinesh Chikkanna, Om V. Singh, Hyunsoo Han*
Department of Chemistry, The University of Texas at San Antonio, 6900 N. Loop 1604 West, San Antonio, TX 78249, USA
Fax: +1(210)4584958; e-Mail: hhan@utsa.edu;
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Publication History

Received 18 April 2003
Publication Date:
30 June 2003 (online)

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Abstract

A new synthetic strategy, which allows a complete stereo­chemical control of all four chiral centers of two important polyhydroxylated pyrrolidines 8 and 9, is described. The cornerstone of the present strategy is a successful implementation of the regioselective asymmetric aminohydroxylation (RAA) reaction of the designed achiral olefin 1 and the intramolecular stereoselective amidomercuration reaction of the δ-alkenylamide 4, which were used for the introduction of the vicinal amino alcohol functionality and for the construction of the five membered ring in the targets respectively.

Key words

carbohydrate - glycosidase inhibitor - polyhydroxylated pyrrolidine - regioselective asymmetric aminohydroxylation reaction - intramolecular amidomercuration reaction

18

The NMR data of 8 and 9 are consistent with those in the literatures (ref. [12j] for 8 and ref. [12m] for 9). For 8, 1H NMR (500 MHz, D2O) δ 3.73-3.77 (m, 2 H), 3.80-3.86 (m, 4 H), 4.20 (d, 2 H, J = 2.0 Hz); 13C NMR (125 MHz, D2O) δ 61.17, 66.58, 78.36. For 9, 1H NMR (500 MHz, D2O) δ 1.27 (d, 3 H, J = 7.0 Hz), 3.75 (dd, 1 H, J = 7.5 Hz, 10.5 Hz), 3.77-3.87 (m, 3 H), 4.06 (d, 1 H, J = 3.5 Hz), 4.26 (d, 1 H, J = 3.5Hz).